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  • 1.
    Afewerki, Samson
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Direct regiospecific and highly enantioselective intermolecular a-allylic alkylation of aldehydes by combination of transition metal and chiral amine catalysts2012Conference paper (Refereed)
    Abstract [en]

    The direct intermolecular regiospecific and highly enantioselective a-allylic alkylation of linear aldehydes by combination of achiral bench stable Pd(0) complexes and simple chiral amines as co-catalysts is disclosed. The co-catalytic asymmetric chemoselective and regiospecific a-allylic alkylation reaction is linked in tandem with in situ reduction to give the corresponding 2-alkyl alcohols with high enantiomeric ratios (up to 98:2 er). It is also an expeditious entry to valuable 2-alkyl substituted hemiacetals and 2-alkyl-butane-1,4-diols.

  • 2.
    Afewerki, Samson
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Breistein, Palle
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Pirttilä, Kristian
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Deiana, Luca
    Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden.
    Dziedzic, Pawel
    Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden.
    Ibrahem, Ismail
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Catalytic Enantioselective beta-Alkylation of alpha,beta-Unsaturated Aldehydes by Combination of Transition-Metal- and Aminocatalysis: Total Synthesis of Bisabolane Sesquiterpenes2011In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 17, no 32, p. 8784-8788Article in journal (Refereed)
    Abstract [en]

    Branching out! The first co-catalytic enantioselective (up to 98:2 e.r.) β-alkylation of α,β-unsaturated aldehydes by combination of simple chiral amine and copper catalysts provides β-branched aldehydes in a one-pot protocol (see scheme). The methodology was applied to the short total syntheses of bisabolane sesquiterpenes (S)-(+)-curcumene, (E)-(S)-(+)-3- dehydrocurcumene and (S)-(+)-tumerone. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  • 3.
    Afewerki, Samson
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Ibrahem, Ismail
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Rydfjord, Jonas
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Breistein, Palle
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Direct Regiospecific and Highly Enantioselective Intermolecular α-Allylic Alkylation of Aldehydes By Combination of Transition Metal and amine Catalysts2012In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 10, p. 2972-2977Article in journal (Refereed)
    Abstract [en]

    The first direct intermolecular regiospecific and highly enantioselective α-allylic alkylation of linear aldehydes by a combination of achiral bench-stable Pd 0 complexes and simple chiral amines as co-catalysts is disclosed. The co-catalytic asymmetric chemoselective and regiospecificα-allylic alkylation reaction is linked in tandem with in situ reduction to give the corresponding 2-alkyl alcohols with high enantiomeric ratios (up to 98:2 e.r.; e.r.=enantiomeric ratio). It is also an expeditious entry to valuable 2-alkyl substituted hemiacetals, 2-alkyl-butane-1,4-diols, and amines. The concise co-catalytic asymmetric total syntheses of biologically active natural products (e.g., Arundic acid) are disclosed. Go organic! Directintermolecular regiospecific and highly enantioselective α-allylic alkylation of linear aldehydes by a combination of achiral bench-stable Pd 0complexes and simple chiral amines as co-catalysts is disclosed (see scheme). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  • 4.
    Anderson, Mattias
    et al.
    AlbaNova Univ Ctr, KTH Royal Inst Technol, Sch Biotechnol, Div Ind Biotechnol, SE-10691 Stockholm, Sweden.
    Afewerki, Samson
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Berglund, Per
    AlbaNova Univ Ctr, KTH Royal Inst Technol, Sch Biotechnol, Div Ind Biotechnol, SE-10691 Stockholm, Sweden.
    Cordova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences. Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden.
    Total Synthesis of Capsaicin Analogues from Lignin-Derived Compounds by Combined Heterogeneous Metal, Organocatalytic and Enzymatic Cascades in One Pot2014In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 356, no 9, p. 2113-2118Article in journal (Refereed)
    Abstract [en]

    The total synthesis of capsaicin analogues was performed in one pot, starting from compounds that can be derived from lignin. Heterogeneous palladium nanoparticles were used to oxidise alcohols to aldehydes, which were further converted to amines by an enzyme cascade system, including an amine transaminase. It was shown that the palladium catalyst and the enzyme cascade system could be successfully combined in the same pot for conversion of alcohols to amines without any purification of intermediates. The intermediate vanillyl-amine, prepared with the enzyme cascade system, could be further converted to capsaicin analogues without any purification using either fatty acids and a lipase, or Schotten-Baumann conditions, in the same pot. An aldol compound (a simple lignin model) could also be used as starting material for the synthesis of capsaicin analogues. Using l-alanine as organocatalyst, vanillin could be obtained by a retro-aldol reaction. This could be combined with the enzyme cascade system to convert the aldol compound to vanillylamine in a one-step one-pot reaction.

  • 5. Bratt, Katarina
    et al.
    Sunnerheim, Kerstin
    Bryngelsson, Susanne
    Fagerlund, Amelie
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Engman, Lars
    Andersson, Rolf E
    Dimberg, Lena H
    Avenanthramides in Oats (Avena Sativa L.) and Structure-Activity Relationships2003In: Journal of Agricultural and Food Chemistry, ISSN 0021-8561, E-ISSN 1520-5118, Vol. 51, no 3, p. 594-600Article in journal (Refereed)
    Abstract [en]

    Eight avenanthramides, amides of anthranilic acid (1) and 5-hydroxyanthranilic acid (2), respectively, and the four cinnamic acids p-coumaric (p), caffeic (c), ferulic (f), and sinapic (s) acid, were synthesized for identification in oat extracts and for structure−antioxidant activity studies. Three compounds (2p, 2c, and 2f) were found in oat extracts. As assessed by the reactivity toward 1,1-diphenyl-2-picrylhydrazyl (DPPH), all avenanthramides except 1p showed activity. Initially, the antioxidant activity of the avenanthramides decreased in a similar order as for the corresponding cinnamic acids, that is: sinapic > caffeic > ferulic > p-coumaric acid. The avenanthramides derived from 2 were usually slightly more active than those derived from 1. All avenanthramides inhibited azo-initiated peroxidation of linoleic acid. 1c and 1s were initially the most effective compounds. The relative order of antioxidant activities was slightly different for the DPPH and the linoleic acid assays run in methanol and chlorobenzene, respectively.

  • 6.
    Breistein, Palle
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Development of highly enantioselective organocatalyzed transformations2011Doctoral thesis, comprehensive summary (Other academic)
  • 7.
    Breistein, Palle
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Johansson, Jonas
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Ibrahem, Ismail
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Lin, S.
    Deiana, Luca
    Sun, J.
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    One-step catalytic enantioselective 5-hydroxy-α-quaternary proline synthesis: An asymmetric entry to highly functionalized α-quaternary proline derivativesManuscript (preprint) (Other academic)
  • 8.
    Cordova, Armando
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Cihalova, Sylva
    Charles Univ Prague, Fac Sci, Dept Organ & Nucl Chem, Prague 12840, Czech Republic .
    Dziedzic, Pawel
    Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden.
    Vesely, Jan
    Charles Univ Prague, Fac Sci, Dept Organ & Nucl Chem, Prague 12840, Czech Republic .
    Asymmetric Aza-Morita-Baylis-Hillman-type reactions: The highly enantioselective reaction between unmodified α,β-unsaturated aldehydes and N-acyl imines by organo-co-catalysis2011In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, ISSN 1615-4150, Vol. 353, no 7, p. 1096-1108Article in journal (Refereed)
    Abstract [en]

    The highly enantioselective organo-co-catalytic aza-Morita-Baylis-Hillman (MBH)-type reaction between N-carbamate-protected imines and alpha,beta-unsaturated aldehydes has been developed. The organic co-catalytic system of proline and 1,4-diazabicyclo[2.2.2]octane (DABCO) enables the asymmetricsynthesis of the corresponding N-Boc- and N-Cbz-protected beta-amino-alpha-alkylidene-aldehydes in good to high yields and up to 99% ee. In the case of aza-MBH-type addition of enals to phenylprop-2-ene-1-imines, the co-catalytic reaction exhibits excellent 1,2-selectivity. The organo-co-catalytic aza-MBH-type reaction can also be performed by the direct highly enantioselective addition of alpha,beta-unsaturated aldehydes to bench-stable N-carbamate-protected alpha-amidosulfones to give the corresponding beta-amino-alpha-alkylidene-aldehydes with up to 99% ee. The organo-co-catalytic aza-MBH-type reaction is also an expeditious entry to nearly enantiomerically pure beta-amino-alpha-alkylidene-amino acids and beta-amino-alpha-alkylidene-lactams (99% ee). The mechanism and stereochemistry of the chiral amine and DABCO co-catalyzed aza-MBH-type reaction are also discussed.

  • 9.
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Catalytic Asymmetric Conjugate Reactions2010Collection (editor) (Other academic)
    Abstract [en]

    Information from publisher:

    This unique and long-awaited handbook on this important topic in the hot field of stereoselective organic synthesis covers several types of nucleophiles. Top international authors deal with modern forms of achieving stereoselective conjugate additions based on the use of chiral ligands or asymmetric catalysis, such as P-N ligands, organocatalysis, domino reactions, Lewis acid and base catalysis. There is also a discussion of the employment of enantioselective conjugate addition transformations in total synthesis of important molecules. With its reliable and previously unpublished experimental procedures, this is a true source of high quality information.

  • 10.
    Córdova, Armando
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Ibrahem, Ismail
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Afewerki, Samson
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Breistein, Palle
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Deiana, Luca
    Zhao, Gui-Ling
    Dziedzic, Pawel
    Pirttilä, Kristian
    Lin, Shuangzheng
    TOC-Trends in Organic Chemistry: Selective Catalysis2010Conference paper (Other academic)
  • 11.
    Córdova, Armando
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    R., Rios
    Aziridine Formation: in C-N Bond Formation2012In: Comprehensive Chirality / [ed] Yamamoto, H.; Carreira, E. Eds, Oxford: Elsevier, 2012Chapter in book (Refereed)
  • 12.
    Deiana, L.
    et al.
    Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden .
    Ghisu, L.
    Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden .
    Córdova, O.
    Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden .
    Afewerki, Samson
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Zhang, Renyun
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden .
    Efficient and highly enantioselective aerobic oxidation-michael- carbocyclization cascade transformations by integrated Pd(0)-CPG nanoparticle/chiral amine relay catalysis2014In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, Vol. 46, no 10, p. 1303-1310Article in journal (Refereed)
    Abstract [en]

    A series of highly diastereo- and enantioselective aerobic oxidation-Michael-carbocyclization cascade transformations by integrated heterogeneous Pd(0)-CPG nanoparticle/chiral amine relay catalysis are disclosed. The heterogeneous Pd(0)-CPG nanoparticle catalysts were efficient for both the sequential aerobic oxidation and dynamic kinetic asymmetric Michael- carbocyclization transformations, resulting in 1) oxidation of a variety of allylic alcohols to enals and 2) formation of cyclopentenes containing an all-carbon quaternary stereocenter in good to high yields with up to 20:1 dr and 99.5:0.5 er. © Georg Thieme Verlag Stuttgart.New York.

  • 13. Deiana, L
    et al.
    Zhao, G-L
    Lin, S
    Dziedzic, P
    Zhang, Q
    Leijonmarck, H
    Còrdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Organocatalytic enantioselective aziridination of α-substituted α,β-unsaturated aldehydes: Asymmetric synthesis of terminal aziridines2010In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 352, no 18, p. 3201-3207Article in journal (Refereed)
    Abstract [en]

    The first example of a highly enantioselective organocatalytic aziridination of α-substituted α,β-unsaturated aldehydes is presented. The reaction is catalyzed by simple chiral amines and gives access to highly functional terminal azirdines containing an α-tertiary amine stereocenter in high yields and enantiomeric ratios (95.5:4.5-98:2)

  • 14.
    Deiana, Luca
    et al.
    Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden .
    Afewerki, Samson
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Palo-Nieto, Carlos
    Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden .
    Verho, Oscar
    Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden .
    Johnston, Eric V
    Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden .
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Highly Enantioselective Cascade Transformations by Merging Heterogeneous Transition Metal Catalysis with Asymmetric Aminocatalysis2012In: Scientific reports, ISSN 2045-2322, Vol. 2, p. Art. no. 851-Article in journal (Refereed)
    Abstract [en]

    The concept of combining heterogeneous transition metal and amine catalysis for enantioselective cascade reactions has not yet been realized. This is of great advantage since it would allow for the recycling of expensive and non-environmentally friendly transition metals. We disclose that the use of a heterogeneous Pd-catalyst in combination with a simple chiral amine co-catalyst allows for highly enantioselective cascadetransformations. The preparative power of this process has been demonstrated in the context of asymmetric cascade Michael/carbocyclizationtransformations that delivers cyclopentenes bearing an all carbon quaternary stereocenters in high yields with up to 30:1 dr and 99% ee. Moreover, a variety of highly enantioselective cascade hetero-Michael/ carbocyclizations were developed for the one-pot synthesis of valuable dihydrofurans and pyrrolidines (up to 98% ee) by using bench-stable heterogeneous Pd and chiral amines as co-catalysts. © 2012 Macmillan Publishers Limited. All rights reserved.

  • 15.
    Deiana, Luca
    et al.
    Stockholm Univ, S-10691 Stockholm, Sweden.
    Cordova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences. Stockholm Univ, S-10691 Stockholm, Sweden.
    Nieto, Carlos Palo
    Stockholm Univ, S-10691 Stockholm, Sweden.
    Jiang, Yan
    Stockholm Univ, S-10691 Stockholm, Sweden.
    Johnston, Eric
    Stockholm Univ, S-10691 Stockholm, Sweden.
    Verho, Oscar
    Stockholm Univ, S-10691 Stockholm, Sweden.
    Combined multistep heterogeneous transition metal catalysis and aminocatalysis for asymmetric cascade reactions2013In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 245, p. Meeting abstract 147-ORGN-Article in journal (Other academic)
  • 16. Deiana, Luca
    et al.
    Zhao, Gui-Ling
    Dziedzic, Pawel
    Rios, Ramon
    Vesely, Jan
    Ekström, Jesper
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    One-pot highly enantioselective catalytic Mannich-type reactions between aldehydes and stable a-amido sulfones: Asymmetric synthesis of b-amino aldehydes and b-amino acids2010In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 51, no 2, p. 234-237Article in journal (Refereed)
    Abstract [en]

    A highly enantioselective catalytic route to carbamate- and benzoate-protected β-amino aldehydes and β-amino acids is presented. The amino acid-catalyzed one-pot asymmetric reaction between unmodified aldehydes and α-amido sulfones gives the corresponding β-amino compounds with up to 95:5 dr and 97–>99% ee.

  • 17.
    Fagerlund, Amelie
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Shanks, David
    Sunnerheim, Kerstin
    Engman, Lars
    Frisell, Håkan
    Protective effects of synthetic and naturally occurring antioxidants in pulp products2003In: Nordic Pulp & Paper Research Journal, ISSN 0283-2631, E-ISSN 2000-0669, Vol. 18, p. 176-181Article in journal (Refereed)
    Abstract [en]

    Various types of natural and synthetic antioxidants when added to handsheets of pulp in low concentrations (0.2% weight%) could significantly reduce the emission of hexanal. The most efficient compounds caused a 90% reduction after eight weeks. Their capacity to inhibit brightness reversion was limited.

  • 18.
    Ibrahem, Ismail
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Afewerki, Samson
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Breistein, Palle
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    One-pot three-component catalytic asymmetric synthesis of homoallylboronates2012In: ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY. Vol 243, American Chemical Society (ACS), 2012, p. 889-INOR-Conference paper (Refereed)
    Abstract [en]

    1. A novel one-pot three-component catalytic enantioselective reaction between bis(pinacolato)diboron, enals and 2-(triphenylphosphoranylidene)acetate esters employing inexpensive bench stable Cu salts and simple chiral amine as co-catalysts is presented. The reaction proceeds via a tandem catalytic asymmetric conjugate borane addition/Wittig sequence where the b-boration step is 1,4-selective and gives the corresponding homoallylboronate products with high enantiomeric ratios (up to 97.5:2.5 er).

    2. The direct intermolecular regiospecific and highly enantioselective a-allylic alkylation of linear aldehydes by combination of achiral bench stable Pd(0) complexes and simple chiral amines as co-catalysts is disclosed. The co-catalytic asymmetric chemoselective and regiospecific a-allylic alkylation reaction is linked in tandem with in situ reduction to give the corresponding 2-alkyl alcohols with high enantiomeric ratios (up to 98:2 er). It is also an expeditious entry to valuable 2-alkyl substituted hemiacetals and 2-alkyl-butane-1,4-diols.

  • 19.
    Ibrahem, Ismail
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Breistein, Palle
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    One-Pot Three-Component Catalytic Enantioselective Synthesis of Homoallylboronates2011In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 50, p. 12036-12041Article in journal (Refereed)
    Abstract [en]

    No longer a simple bor(ation): The title reaction between bis(pinacolato)diboron, enals, and 2-(triphenylphosphoranylidene)acetates employing bench-stable copper salts and a simple chiral amine co-catalyst is presented. The reaction proceeds through a catalytic asymmetric conjugate borane addition/Wittig sequence wherein the β-boration step is 1,4-selective and gives the corresponding homoallylboronate products with high enantiomeric ratios.

  • 20.
    Ibrahem, Ismail
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Breistein, Palle
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    One-pot three-component highly selective synthesis of homoallylboronates by using metal-free catalysis2012In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 17, p. 5175-5179Article in journal (Refereed)
    Abstract [en]

    Metal-free selectivity: The first metal-free one-pot three-component highly chemo- and regioselective catalytic synthesis of homoallylboranes using simple N-heterocyclic carbenes (NHC) and amines is presented. The catalytic reaction between B 2(pin) 2, α,β-unsaturated aldehydes and 2-(triphenylphosphoranylidene)acetate esters proceeds through a catalytic metal-free β-boration/Wittig cascade sequence (see scheme). © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  • 21.
    Ibrahem, Ismail
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Ma, Guangning
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Afewerki, Samson
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Palladium/Chiral Amine Co-catalyzed Enantioselective beta-Arylation of alpha,beta-Unsaturated Aldehydes2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 3, p. 878-882Article in journal (Refereed)
    Abstract [en]

    Palladium and a simple chiral amine are used as co-catalysts for the enantioselective conjugate addition of aryl boronic acids to α,β-unsaturated aldehydes (see scheme). The synthetic utility of this co-catalyzed reaction was demonstrated in the short total syntheses of (R)-(-)-curcumene and 4-aryl-2-ones. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  • 22.
    Ibrahem, Ismail
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Santoro, Stefano
    Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden.
    Himo, Fahmi
    Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden.
    Cordova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Enantioselective Conjugate Silyl Additions to alpha,beta-Unsaturated Aldehydes Catalyzed by Combination of Transition Metal and Chiral Amine Catalysts2011In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 353, no 2-3, p. 245-252Article in journal (Refereed)
    Abstract [en]

    We report that transition metal-catalyzed nucleophilic activation can be combined with chiral amine-catalyzed iminium activation as exemplified by the unprecedented enantioselective conjugate addition of a dimethylsilanyl group to alpha,beta-unsaturated aldehydes. These reactions proceed with excellent 1,4-selectivity to afford the corresponding beta-silyl aldehyde products 3 in high yields and up to 97:3 er using inexpensive bench stable copper salts and simple chiral amine catalysts. The reaction can also generate a quaternary stereocenter with good enantioselectivity. Density functional calculations are performed to elucidate the reaction mechanism and the origin of enantioselectivity.

  • 23.
    Jiang, Yan
    et al.
    Stockholm University, Stockholm.
    Deiana, Luca
    Stockholm University, Stockholm.
    Alimohammadzadeh, Rana
    Stockholm University, Stockholm.
    Liu, Leifeng
    Stockholm University, Stockholm.
    Sun, Junliang
    Stockholm University, Stockholm.
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences. Stockholm University, Stockholm.
    Highly Diastereo- and Enantioselective Cascade Synthesis of Bicyclic Lactams in One-Pot2018In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2018, no 9, p. 1158-1164Article in journal (Refereed)
    Abstract [en]

    A versatile and highly stereoselective synthetic route to functionalized bi- and tricyclic lactams (up to > 20:1 dr and 99 % ee) in one pot from simple starting materials (allylic alcohols, enals, diamines and amino alcohols) using cascade transformations promoted by chiral amine/Brønsted or metal/chiral amine/Brønsted relay catalysis is disclosed. Here molecular oxygen is employed as the terminal oxidant for the latter relay catalysis approach. 

  • 24. Lin, S
    et al.
    Zhao, G-L
    Deiana, L
    Sun, J
    Zhang, Q
    Leijonmarck, H
    Còrdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Dynamic kinetic asymmetric domino oxa-michael/carbocyclization by combination of transition-metal and amine catalysis: Catalytic enantioselective synthesis of dihydrofurans2010In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, no 47, p. 13930-13934Article in journal (Refereed)
    Abstract [en]

    Into the pot: A one-pot highly chemo- and enantioselective catalytic domino oxa-Michael/carbocyclization between α,β-unsaturated aldehydes and propargylic alcohols is presented. This dynamic kinetic transformation requires a combination of transition-metal and amine catalysis to afford functionalized dihydrofurans in good to high yields and up to 99.5:0.5 e.r.

  • 25.
    Ma, Guangning
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Afewerki, Samson
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Deiana, L.
    Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden .
    Palo-Nieto, C.
    Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden .
    Liu, L.
    Berzelii Center EXSELENT, Stockholm University, Sweden .
    Sun, J.
    Berzelii Center EXSELENT, Stockholm University, Sweden .
    Ibrahem, Ismail
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    A palladium/chiral amine co-catalyzed enantioselective dynamic cascade reaction: Synthesis of polysubstituted carbocycles with a quaternary carbon stereocenter2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 23, p. 6050-6054Article in journal (Refereed)
    Abstract [en]

    Polysubstituted 5- and 6-membered carbocycles were synthesized by the title reaction. The one-pot dynamic relay process generates four new stereocenters, including a quaternary carbon center, in a highly enantioselective fashion (99.5:0.5→99:0.5 e.r.) by using a simple combination of palladium and chiral amine co-catalysts. 

  • 26.
    Ma, Guangning
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Bartoszewicz, Agnieszka
    Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden .
    Ibrahem, Ismail
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Highly Enantioselective Co-Catalytic Direct Aldol reactions by Combination of Hydrogen-Bond Donating and Acyclic Amino Acid Catalysts2011In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 353, no 17, p. 3114-3122Article in journal (Refereed)
    Abstract [en]

    Highly enantioselective co-catalytic direct aldol reactions by a combination of simple hydrophobic acyclic amino acid and hydrogen-bond donating catalysts are presented. The corresponding aldol products are formed in high yields with high regio-, diastereo- (anti or syn) and enantioselectivity (up to 99.5:0.5 er). The catalyst loadings can be decreased to as little as 2 mol%.

  • 27.
    Ma, Guangning
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Lin, Shuangzheng
    Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden .
    Ibrahem, Ismail
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Kubik, Grzegorz
    Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden .
    Liu, Leifeng
    Stockholm Univ, Dept Mat & Environm Chem, Arrhenius Lab, S-10691 Stockholm, Sweden.
    Sun, Junliang
    Stockholm Univ, Dept Mat & Environm Chem, Arrhenius Lab, S-10691 Stockholm, Sweden.
    Cordova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Achiral Co-Catalyst Induced Switches in Catalytic Asymmetric Reactions on Racemic Mixtures (RRM): From Stereodivergent RRM to Stereoconvergent Deracemization by Combination of Hydrogen Bond Donating and Chiral Amine Catalysts2012In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 354, no 14-15, p. 2865-2872Article in journal (Refereed)
    Abstract [en]

    A stereochemical divergent approach for the highly enantioselective synthesis of distinct bicyclic products with multiple stereocenters from a racemate using a single chiral catalyst is disclosed. It is based on switches of the overall reaction pathways in the chiral amine-catalyzed cascade reactions between racemic ?-nitro ketones and a,beta-unsaturated aldehydes using different achiral co-catalysts. The utility of the method is exemplified by the highly diasteroselective switch and stereoconvergent deracemization process by combination of chiral amine and achiral hydrogen-bond-donating catalysts.

  • 28.
    Nieberding, Caroline M
    et al.
    Evolutionary Biology Group, Institute of Biology, Leiden University, 2300 RA Leiden, Netherlands.
    Fischer, Klaus
    Zoological Institute and Museum, Greifswald University, Johann-Sebastian-Bach Str. 11/12, 17489 Greifswald, Germany.
    Saastamoinen, Marjo
    Metapopulation Research Group, Department of BioSciences, University of Helsinki, PO Box 65 (Viikinkaari 1), FI-00014, Finland.
    Allen, Cerisse E
    Division of Biological Sciences, University of Montana, Missoula MT 59812, United States.
    Wallin, Erika A.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Brakefield, Paul M
    University Museum of Zoology Cambridge, Downing Street, Cambridge, CB2 3EJ, United Kingdom.
    Cracking the olfactory code of a butterfly: the scent of ageing.2012In: Ecology Letters, ISSN 1461-023X, E-ISSN 1461-0248, Vol. 15, no 5, p. 415-424Article in journal (Refereed)
    Abstract [en]

    Ecology Letters (2012) 15: 415-424 ABSTRACT: Although olfaction is a primary mode of communication, its importance in sexual selection remains understudied. Here, using the butterfly Bicyclus anynana, we address all the parameters of importance to sexual selection for a male olfactory signal. We show that variation in the male sex pheromone composition indicates male identity and male age. Courting males of different ages display small absolute (c. 200 ng) but large relative (100%) change of one specific pheromone component (hexadecanal) which, unlike the other components, showed no heritability. Females prefer to mate with mid-aged over younger males and the pheromone composition is sufficient to determine this preference. Surprisingly refined information is thus present in the male olfactory signal and is used for sexual selection. Our data also reveal that there may be no 'lek paradox' to resolve once the precise signal of importance to females is identified, as hexadecanal is, as expected, depleted in additive genetic variation.

  • 29.
    Nilsson, Anna
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Identification and Syntheses of Semiochemicals Affecting Mnesampela privata and Trioza apicalis2009Licentiate thesis, comprehensive summary (Other academic)
    Abstract [en]

    The Autumn gum moth, Mnesampela privata (Lepidoptera: Geometridae) is an endemic Australian moth whose larvae feed upon species of Eucalyptus. The moths favorite host plants are E. globulus and E. nitens which are the most important species used in commercial plantations of the Australian pulpwood industry. The autumn gum moth has become one of the most significant outbreak insects of eucalyptus plantations throughout Australia. As a consequence great financial losses to the forest industry occur. Today insecticides such as pyrethroids are used for control of eucalyptus defoliators as M. privata.

    The carrot psyllid, Trioza apicalis (Homoptera: Psylloidea), is one of the major pests of carrot (Daucus carota) in northern Europe. The psyllid causes curling of the carrot leafs and reduction of plant growth. Today the carrot crops are protected with the pyrethroid insecticide cypermethrin, which is toxic to aquatic organisms and is, from 2010, prohibited for use in Sweden by the Swedish Chemicals Inspectorate.

    An alternative to insecticides is to protect the seedlings with semiochemicals, a chemical substance or mixture of them that carries a message. This thesis describes the identification and the syntheses of semiochemicals from the above mentioned insect species.

    From analysis of abdominal tip extracts of M. privata females from Tasmania a blend of (3Z,6Z,9Z)-3,6,9-nonadecatriene and (3Z,6Z,9Z)-3,6,9-heneicosatriene was identified as the sex pheromone of this species. The identification of the C19- and C21-trienes was confirmed by synthesis.

    In the analysis of carrot leaf extracts we found a compound, α-cis-bergamotene, that induces antennal response in the carrot psyllid. This is just the beginning of the studies of trying to manipulate this psyllid with semiochemicals instead of insecticides.

  • 30.
    Norgren, Magnus
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Edlund, Håkan
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Lignin: Recent advances and emerging applications2014In: Current Opinion in Colloid & Interface Science, ISSN 1359-0294, E-ISSN 1879-0399, Vol. 19, p. 409-416Article, review/survey (Refereed)
    Abstract [en]

    In this paper, we focus on the recent advances on the physical chemistry of lignin. Emerging trends of incorporating lignin in promising future applications such as controlled release, saccharification of lignocelluloses, bioplastics, composites, nanoparticles, adsorbents and dispersants, in electro-chemical applications and carbon fi bers, arealso reviewed. We briefl y describe the complexity of the lignin structure that influences the solution behavior, both as a macromolecule and a col loid, as well as the potential of being a renewable precursor in the development of high-value applications. Special attention is paid on summarizing the present knowledge on lignin colloidalstability and surface chemistry.

  • 31. Nozière, Barbara
    et al.
    Dziedzic, Pawel
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Common Inorganic Ions Catalyze Chemical Reactions of Organic Compounds in Atmospheric Aerosols2010In: Physical Chemistry, Chemical Physics - PCCP, ISSN 1463-9076, E-ISSN 1463-9084, Vol. 12, p. 3864-Article in journal (Refereed)
  • 32. Rios, R
    et al.
    Schyman, P
    Sundén, H
    Zhao, G-L
    Ullah, F
    Chen, L-J
    Laaksonen, A
    Còrdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Nonlinear effects in asymmetric amino acid catalysis by multiple interconnected stereoselective catalytic networks2010In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, no 47, p. 13935-13940Article in journal (Refereed)
    Abstract [en]

    A fine line: The generation of significant positive nonlinear effects in asymmetric amino acid catalysis under homogeneous conditions, which can be explained by the model for cooperative catalytic stereoselective pathways, is reported. The addition of an achiral aldehyde generated the multiple interconnected stereoselective catalytic network.

  • 33.
    Shuangzheng, Lin
    et al.
    Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden .
    Deiana, Luca
    Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden .
    Tseggai, Abrehet
    Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden .
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Concise Total Synthesis of Dihydrocorynanthenol, Protoemetinol, Protoemetine, 3-epi-Protoemetinol and Emetine2012In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 2, p. 398-408Article in journal (Refereed)
    Abstract [en]

    A concise asymmetric assembly of secologanine tryptamine and dopamine alkaloids by means of a one-pot three-component cascade reaction methodology is disclosed. This is demonstrated by the expeditious total syntheses of (-)-dihydrocorynanthenol, (-)-protoemetinol, (-)-protoemetine, (-)-3-epi-protoemetinol, and emetine (3-6 steps). The biomimetic synthetic strategy involved the following key steps: (i) One-pot three-component highly enantioselective catalytic Michael/Pictet-Spengler/lactamization cascade reactions; (ii) One-pot tandem Swern oxidation/Wittig sequences; (iii) One-pot tandem hydrogenation sequences.

  • 34.
    Shuangzheng, Lin
    et al.
    Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden.
    Tseggai, Abrehet
    Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden.
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design.
    Concise catalytic asymmetric total synthesis of biologically active tropane alkaloids2012In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 354, no 7, p. 1363-1372Article in journal (Refereed)
    Abstract [en]

    A general strategy for the total asymmetric synthesis of valuable tropane alkaloids by catalytic stereoselective transformations is disclosed. The power of this approach is exemplified by the concise catalytic enantioselective total syntheses of (+)-methylecgonine, (-)-cocaine and (+)-cocaine as well as the first catalytic asymmetric total syntheses of a cocaine C-1 derivative and (+)-ferruginine starting from 5-oxo-protected-α,β-unsaturated enals using only two and three column chromatographic purification steps, respectively. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  • 35.
    Sjöberg, Natalia
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    (S)-1,2,3,4-tetrahydroisoquinoline derived chiral auxiliary in diastereoselective alkylationManuscript (preprint) (Other academic)
    Abstract [en]

    A novel chiral auxiliary (S)-2-(1,2,3,4-tetrahydroisoquinolin-3-yl)propan-2-ol 1 was synthesized from (S)-1,2,3,4-tetrahydroisoquinoline acid 2. Alkylation of the propanoylated chiral auxiliary (S)-1-(3-(2-hydroxypropan-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)-propan-1-one 3 with benzyl bromide or n-butyl iodide caused moderate to high conversion (42–99%) and moderate diastereomeric ratios (up to 89:11). The major diastereomer obtained in the reaction with benzyl bromide was (R,S). Some of the reactions were carried out with LiCl as an enolate coordinating agent, which affected conversion and diastereomeric ratio negatively. 

  • 36.
    Sjöberg, Natalia
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
    Structure determination and synthesis of natural extracts. (S)-1,2,3,4-tetrahydroisoquinoline derived chiral auxiliary in diastereoselective alkylation: Licentiate thesisManuscript (preprint) (Other academic)
  • 37. Walker, P W
    et al.
    Allen, G R
    Davies, N W
    Smith, J A
    Molesworth, P P
    Nilsson, Anna
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Andersson, Fredrik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Identification, Synthesis and Field Testing of (3Z,6Z,9Z)-3,6,9-Henicosatriene, a Second Bioactive Component of the Sex Pheromone of the Autumn Gum Moth, Mnesampela privata2009In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 35, no 12, p. 1411-1422Article in journal (Refereed)
    Abstract [en]

    Abstract - The sex pheromone of Mnesampela privata, an endemic pest of Eucalyptus plantations in Australia, was previously identified as containing a single bioactive compound, (3Z,6Z,9Z)-3,6,9-nonadecatriene (C19 triene). Initial field testing of lures containing 1, 5 or 10 mg of C19 triene (>98% purity) caught no or very few male M. privata. (3Z,6Z,9Z)-3,6,9-Henicosatriene (C21 triene) was identified as an additional minor pheromone component in abdominal tip extracts of M. privata females from Tasmania. Levels of C19 and C21 trienes extracted from individual females varied greatly, but the ratio was relatively constant at 33:1. Electroantennograms (EAG) of synthetic C21 triene with male M. privata gave positive but consistently lower responses than elicited by the C19 triene. Field tests showed that the addition of 1-6% C21 triene to 1mg C19 triene significantly increased trap catch and the detection of M. privata in plantations. Traps baited with a 16:1 ratio caught significantly more moths than those baited with a ratio approximating that of females.

  • 38. Zhao, Gui-Ling
    et al.
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    ECAs of Organolithium reagents, Grignard reagents and Examples of Cu-Catalyzed ECAs2010In: Catalytic Asymmetric Conjugate Reactions, Wiley-VCH Verlagsgesellschaft, 2010Chapter in book (Refereed)
  • 39. Zhao, Gui-Ling
    et al.
    Hafrén, Jonas
    Deiana, Luca
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Heterogeneous “Organoclick” Derivatization of Polysaccharides: Photochemical Thiol-Ene Click Modification of Solid Cellulose2010In: Macromolecular rapid communications, ISSN 1022-1336, E-ISSN 1521-3927, Vol. 31, no 8, p. 740-744Article in journal (Refereed)
  • 40. Zhao, Gui-Ling
    et al.
    Ullah, Farman
    Deiana, Luca
    Lin, Shuangzheng
    Zhang, Qiong
    Sun, Junliang
    Ibrahem, Ismail
    Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University,.
    Dziedzic, Pawel
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Dynamic kinetic asymmetric transformation (DYKAT) by combined amine and transition metal catalyzed enantioselective cycloisomerization2010In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765Article in journal (Refereed)
  • 41. Zhu, Mingzhao
    et al.
    Shuangzheng, Lin
    Zhao, Gui-Ling
    Sun, Junliang
    Córdova, Armando
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Organocatalytic diasteroselective dibromination of alkenes2010In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 51, p. 2708-2712Article in journal (Refereed)
    Abstract [en]

    A highly diastereoselective pyrrolidine-promoted dibromination of alkenes by combination of NBS and succinimide is presented. The pyrrolidine-mediated dibromination of alkenes is higly anti-selective and gives the corresponding products in moderate to high yields and up to >25:1 dr.

1 - 41 of 41
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