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  • 1.
    Alamsetti, Santosh Kumar
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Persson, Andreas K. A.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Palladium-Catalyzed Intramolecular Hydroamination of Propargylic Carbamates and Carbamothioates2014Inngår i: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 16, nr 5, s. 1434-1437Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    An efficient and simple methodology was developed for the synthesis of oxazolidinones, oxazolidinthiones, imidazolidinthiones, and imidazolidinones from the corresponding propargylic starting materials using Pd(OAc)(2) and n-Bu4NOAc as catalysts in DCE at room temperature.

  • 2. Alexakis, A.
    et al.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Krause, N.
    Pàmies, O.
    Diéguez, M.
    Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions2008Inngår i: Chemical Reviews, ISSN 0009-2665, Vol. 108, nr 8, s. 2796-2823Artikkel i tidsskrift (Fagfellevurdert)
  • 3.
    Bartholomeyzik, Teresa
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Mazuela, Javier
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Pendrill, Robert
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Deng, Youqian
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Palladium-Catalyzed Oxidative Arylating Carbocyclization of Allenynes: Control of Selectivity and Role of H2O2014Inngår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 53, nr 33, s. 8696-8699Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Highly selective protocols for the carbocyclization/arylation of allenynes using arylboronic acids are reported. Arylated vinylallenes are obtained with the use of BF3 center dot Et2O as an additive, whereas addition of water leads to arylated trienes. These conditions provide the respective products with excellent selectivities (generally > 97:3) for a range of boronic acids and different allenynes. It has been revealed that water plays a crucial role for the product distribution.

  • 4.
    Bermejo Gómez, Antonio
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Holmberg, Pär
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Martin-Matute, Belén
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Transition metal-catalyzed redox isomerization of codeine and morphine in water2014Inngår i: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 4, nr 74, s. 39519-39522Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A water-soluble rhodium complex formed from commercially available [Rh(COD)(CH3CN)(2)]BF4 and 1,3,5-triaza-7-phosphaadamantane (PTA) catalyzes the isomerization of both codeine and morphine into hydrocodone and hydromorphone with very high efficiency. The reaction is performed in water, allowing isolation of the final products by simple filtration, which results in very high isolated yields. The reactions can be easily scaled up to 100 g.

  • 5. Berner, Simon
    et al.
    Lidbaum, Hans
    Ledung, Greger
    Åhlund, John
    Nilson, Katharina
    Schiessling, Joachim
    Gelius, Ulrik
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Puglia, Carla
    Oscarsson, Sven
    Electronic and structural studies of immobilized thiol-derivatized cobalt porphyrins on gold surfaces2007Inngår i: Applied Surface Science, ISSN 0169-4332, Vol. 253, nr 18, s. 7540-7548Artikkel i tidsskrift (Fagfellevurdert)
  • 6. Bogár, Krisztián
    et al.
    Krumlinde, Patrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Hydrogenized Wilkinson´s Catalyst for Transfer Hydrogenation of Carbonyl CompoundsManuskript (preprint) (Annet vitenskapelig)
    Abstract [en]

    Combining the advantages of homogeneous and heterogeneous catalysis is possible by heterogenization of homogeneous transition metal complexes based on a grafting/anchoring technique. Wilkinson’s catalyst ((RhCl(PPh3)3) immobilized on common silica showed high activity and selectivity in transfer hydrogenation reactions of different carbonyl compounds in isopropanol. Reactions conducted at reflux in isopropanol afforded the corresponding carbinols in high yields in short reaction times. The heterogeneous feature of the catalyst allows easy recovery and efficient reuse in the same reaction up to 5 times without loss of catalytic activity.

  • 7. Bogár, Krisztián
    et al.
    Martín-Matute, Belén
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Large-scale ruthenium- and enzyme-catalyzed dynamic kinetic resolution of (rac)-1-phenylethanol2007Inngår i: Beilstein Journal of Organic Chemistry, ISSN 1860-5397, Vol. 3, s. artikel nr 50-Artikkel i tidsskrift (Fagfellevurdert)
  • 8.
    Borén, Linnéa
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Leijondahl, Karin
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Dynamic Kinetic Asymmetric Transformation of 1,4-diols and Preparation of Trans-2,5-Disubstituted pyrrolidines2009Inngår i: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 50, nr 26, s. 3237-3240Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Dynamic kinetic asymmetric transformation (DYKAT) of a series of 1,4-diols is carried out with Candida antarctica lipase B (CALB), Pseudomonas cepacia lipase II (PS-C II), and a ruthenium catalyst. A β-chloro-substituted 1,4-diol is successfully transformed into an optically pure 1,4-diacetate, which is a highly useful synthetic intermediate. The usefulness of the optically pure 1,4-diacetates is demonstrated by the synthesis of enantiopure 2,5-disubstituted pyrrolidines.

  • 9.
    Borén, Linnéa
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Martín-Matute, Belén
    Xu, Yongmei
    Córdova, Armando
    Bäckvall, Jan-Erling
    (S)-Selective Kinetic Resolution and Chemoenzymatic Dynamic Kinetic Resolution of Secondary Alcohols2006Inngår i: Chemistry: a European Journal, ISSN 0947-6539, Vol. 12, nr 1, s. 225-232Artikkel i tidsskrift (Fagfellevurdert)
  • 10. Bratt, Emma
    et al.
    Verho, Oscar
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Johansson, Magnus J.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    A General Suzuki Cross-Coupling Reaction of Heteroaromatics Catalyzed by Nanopalladium on Amino-Functionalized Siliceous Mesocellular Foam2014Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 79, nr 9, s. 3946-3954Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Suzuki-Miyaura cross-coupling reactions of heteroaromatics catalyzed by palladium supported in the cavities of amino-functionalized siliceous mesocellular foam are presented. The nanopalladium catalyst effectively couples not only heteroaryl halides with boronic acids but also heteroaryl halides with boronate esters, potassium trifluoroborates, MIDA boronates, and triolborates, producing a wide range of heterobiaryls in good to excellent yields. Furthermore, the heterogeneous palladium nanocatalyst can easily be removed from the reaction mixture by filtration and recycled several times with minimal loss in activity. This catalyst provides an alternative, environmentally friendly, low-leaching process for the preparation of heterobiaryls.

  • 11.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. -.
    Asymmetric Catalysis via Dynamic Kinetic Resolution2007Inngår i: Asymmetric Synthesis - The Essentials, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim , 2007, s. 171-175Kapittel i bok, del av antologi (Fagfellevurdert)
    Abstract [en]

    -

  • 12.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Catalytic asymmetric synthesis via combined metal and enzyme catalysis2009Inngår i: 3rd Hellenic Symposium on Organic Synthesis, October 15-17, 2009, Athens, Greece: Abstracts of papers, Athens, 2009Konferansepaper (Annet vitenskapelig)
  • 13.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Modern Oxidation Methods2010Collection/Antologi (Annet vitenskapelig)
  • 14.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Palladium- and ruthenium-catalyzed redox reactions in selective organic synthesis2009Inngår i: Abstract of LOST II Symposium in honour of Prof. Alain Krief, March 18-20, 2009, Namur, Belgium, 2009Konferansepaper (Annet vitenskapelig)
  • 15.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Pd- and Ru-catalyzed redox reactions in catalysis. Application to the combination with enzyme catalysis2009Inngår i: Abstract of 42nd Jahrestreffen Deutscher Katalytiker, March 11-13, 2009, Weimar, Germany, 2009Konferansepaper (Annet vitenskapelig)
  • 16.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Preface2010Inngår i: Topics in catalysis, ISSN 1022-5528, E-ISSN 1572-9028, Vol. 53, nr 13-14, s. 831-831Artikkel i tidsskrift (Fagfellevurdert)
  • 17.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Recent advances in the combination of metal and enzyme catalysis2009Inngår i: Abstract of the 10th Netherlands Catalysis and Chemistry Conference (NCCC-X), March 2-4, 2009, Noordwijkerhout, the Netherlands, 2009Konferansepaper (Annet vitenskapelig)
  • 18.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Selective oxidation of amines and sulfides2010Inngår i: Modern Oxidation Methods / [ed] Jan-Erling Bäckvall, Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA , 2010, 2, s. 277-313Kapittel i bok, del av antologi (Annet vitenskapelig)
  • 19. Carballeira, José Daniel
    et al.
    Krumlinde, Patrik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bocola, Marco
    Vogel, Andreas
    Reetz, Manfred T.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Directed evolution and axial chirality: optimization of the enantioselectivity of Pseudomonas aeruginosa lipase towards the kinetic resolution of a racemic allene2007Inngår i: Chemical Communications, ISSN 1359-7345, Vol. 20, s. 1913-1915Artikkel i tidsskrift (Fagfellevurdert)
  • 20.
    Csjernyik, Gábor
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Notheisz, Ferenc
    Zsigmond, Ágnes
    Ruthenium-Catalyzed Aerobic Oxidation of Alcohols on Zeolite-Encapsulated Cobalt Salophen Catalyst2002Inngår i: Topics in catalysis, ISSN 1022-5528, Vol. 19, nr 1, s. 119-124Artikkel i tidsskrift (Fagfellevurdert)
  • 21.
    Csjernyik, Gábor
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Éll, Alida H
    Fadini, Luca
    Pugin, Benoit
    Efficient Ruthenium-Catalyzed Aerobic Oxidation of Alcohols Using a Biomimetic Coupled Catalytic System2002Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, Vol. 67, nr 5, s. 1657-1662Artikkel i tidsskrift (Fagfellevurdert)
  • 22.
    Deska, Jan
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Enzymatic kinetic resolution of primary allenic alcohols. Application to the total synthesis and stereochemical assignment of striatisporolide A2009Inngår i: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 7, nr 17, s. 3379-3381Artikkel i tidsskrift (Fagfellevurdert)
  • 23.
    Deska, Jan
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    del Pozo Ochoa, Carolina
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Chemoenzymatic dynamic kinetic resolution of axially chiral allenes2010Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, nr 15, s. 4447-4451Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Dimeric palladium bromide complexes bearing monodentate N-heterocyclic carbene ligands have been identified as efficient catalysts for the chemoselective racemization of axially chiral allenyl alcohols. In combination with porcine pancreatic lipase as biocatalyst, a dynamic kinetic resolution has been developed, giving access to optically active allenes in good yield and high enantiomeric purity (

  • 24.
    Engelmark Cassimjee, Karim
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kadow, Maria
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Wikmark, Ylva
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Svedendahl Humble, Maria
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Rothstein, M. L.
    Rothstein, D. M.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    A general protein purification and immobilization method on controlled porosity glass: biocatalytic applications2014Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 50, nr 65, s. 9134-9137Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A general combined purification and immobilization method to facilitate biocatalytic process development is presented. The support material, EziG (TM), is based on controlled porosity glass (CPG) or polymer-coated versions thereof (HybCPG) and binds protein affinity tags. Biocatalytic reactions in aqueous and organic media with seven enzymes of biocatalytic interest are shown.

  • 25.
    Engström, Karin
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Nyhlén, Jonas
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Sandström, Anders G.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Directed evolution of an enantioselective lipase with broad substrate scope for hydrolysis of α-substituted esters2010Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 132, nr 20, s. 7038-7042Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A variant of Candida antarctica lipase A (CalA) was developed for the hydrolysis of α-substituted p-nitrophenyl esters by directed evolution. The E values of this variant for 7 different esters was 45−276, which is a large improvement compared to 2−20 for the wild type. The broad substrate scope of this enzyme variant is of synthetic use, and hydrolysis of the tested substrates proceeded with an enantiomeric excess between 95−99%. A 30-fold increase in activity was also observed for most substrates. The developed enzyme variant shows (R)-selectivity, which is reversed compared to the wild type that is (S)-selective for most substrates.

  • 26.
    Engström, Karin
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Nyhlén, Jonas
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Sandström, Anders G.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Enantioselective Kinetic Resolution of p-Nitrophenyl 2-Phenylpropanoate by a Variant of Candida antarctica Lipase A Developed by Directed Evolution2010Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 132, nr 20, s. 7038-7042Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A variant of Candida antarctica lipase A (CalA) was developed for the hydrolysis of α-substituted p-nitrophenyl esters by directed evolution. The E values of this variant for 7 different esters was 45−276, which is a large improvement compared to 2−20 for the wild type. The broad substrate scope of this enzyme variant is of synthetic use, and hydrolysis of the tested substrates proceeded with an enantiomeric excess between 95−99%. A 30-fold increase in activity was also observed for most substrates. The developed enzyme variant shows (R)-selectivity, which is reversed compared to the wild type that is (S)-selective for most substrates.

  • 27.
    Ericsson, Daniel J.
    et al.
    1Department of Cell and Molecular Biology, Uppsala University, Biomedical Center.
    Kasrayan, Alex
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Johansson, Patrik
    1Department of Cell and Molecular Biology, Uppsala University, Biomedical Center.
    Bergfors, Terese
    1Department of Cell and Molecular Biology, Uppsala University, Biomedical Center.
    Sandström, Anders G.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Mowbray, Sherry L.
    Department of Molecular Biology, Swedish University of Agricultural Sciences, Biomedical Center.
    X-Ray structure of Candida antarctica lipase A shows a novel lid structure and a likely mode of interfacial activation2008Inngår i: Journal of Molecular Biology, ISSN 0022-2836, Vol. 376, nr 1, s. 109-119Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    In nature, lipases (EC 3.1.1.3) catalyze the hydrolysis of triglycerides to form glycerol and fatty acids. Under the appropriate conditions, the reaction is reversible, and so biotechnological applications commonly make use of their capacity for esterification as well as for hydrolysis of a wide variety of compounds. In the present paper, we report the X-ray structure of lipase A from Candida antarctica, solved by single isomorphous replacement with anomalous scattering, and refined to 2.2-Å resolution. The structure is the first from a novel family of lipases. Contrary to previous predictions, the fold includes a well-defined lid as well as a classic α/β hydrolase domain. The catalytic triad is identified as Ser184, Asp334 and His366, which follow the sequential order considered to be characteristic of lipases; the serine lies within a typical nucleophilic elbow. Computer docking studies, as well as comparisons to related structures, place the carboxylate group of a fatty acid product near the serine nucleophile, with the long lipid tail closely following the path through the lid that is marked by a fortuitously bound molecule of polyethylene glycol. For an ester substrate to bind in an equivalent fashion, loop movements near Phe431 will be required, suggesting the primary focus of the conformational changes required for interfacial activation. Such movements will provide virtually unlimited access to solvent for the alcohol moiety of an ester substrate. The structure thus provides a basis for understanding the enzyme's preference for acyl moieties with long, straight tails, and for its highly promiscuous acceptance of widely different alcohol and amine moieties. An unconventional oxyanion hole is observed in the present structure, although the situation may change during interfacial activation

  • 28. Eriksson, Kristofer L.E.
    et al.
    Chow, Winnie W.Y.
    Puglia, Carla
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Göthelid, Emmanuelle
    Oscarsson, Sven
    Performance of a biomimetic oxidation catalyst immobilized on silicon wafers: comparison with its gold congener2010Inngår i: Langmuir, ISSN 0743-7463, E-ISSN 1520-5827, Vol. 26, nr 21, s. 16349-16354Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    With the aim of extending the usefulness of an existing biomimetic catalytic system, cobalt porphyrin catalytic units with thiol linkers were heterogenized via chemical grafting to silicon wafers and utilized for the catalytic oxidation of hydroquinone to p-benzoquinone. Atomic force microscopy (AFM) and X-ray photoelectron spectroscopy (XPS) were used to analyze the morphology and composition of the heterogeneous catalyst. The results of the catalytic oxidation of hydroquinone obtained with porphyrins grafted on silicon were compared with those obtained earlier with the same catalyst in homogeneous phase and immobilized on gold. It was found that the catalysis could run over 400 h, without showing any sign of deactivation. The measured catalytic activity is at least 10 times higher than that measured under homogeneous conditions, but also 10 times lower than that observed with the catalytic unit immobilized on gold. The reasons of this discrepancy are discussed in term of substrate influence and overlayer organization. The silicon-immobilized catalyst has potential as an advanced functional material with applications in oxidative heterogeneous catalysis of organic reactions, as it combines long-term relatively high activity with low cost.

  • 29.
    Fransson, Ann-Britt L.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Borén, Linnéa
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Pàmies, Oscar
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kinetic Resolution and Chemoenzymatic Dynamic Kinetic Resolution of Functionalized γ-Hydroxy Amides2005Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 70, nr 7, s. 2582-2587Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    An efficient kinetic resolution of racemic gamma-hydroxy amides 1 was performed via Pseudomas cepacia lipase (PS-C)-catalyzed transesterification. The enzyme PS-C tolerates both variation in the chain length and different functionalities giving good to high enantioselectivity (E values of up to > 250). The combination of enzymatic kinetic resolution with a ruthenium-catalyzed racemization led to a dynamic kinetic resolution. The use of 2,4-dimethyl-3-pentanol as a hydrogen source to suppress ketone formation in the dynamic kinetic resolution yields the corresponding acetates in good yield and good to high enantioselectivity (ee's up to 98%). The synthetic utility of this procedure was illustrated by the practical synthesis of the versatile intermediate gamma-lactone (R)-5-methyltetrahydrofuran-2-one.

  • 30.
    Fransson, Ann-Britt L.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Leijondahl, Karin
    Bäckvall, Jan-Erling
    Highly Efficient Ru-catalyzed Transfer Hydrogenation/Hydrogenation Procedure for 1,3-Cycloalkandiols using Controlled Microwave HeatingManuskript (Annet vitenskapelig)
  • 31.
    Fransson, Ann-Britt L.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Xu, Yongmei
    Leijondahl, Karin
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Enzymatic Resolution, Desymmetrization and Dynamic Kinetic Asym-metric Transformation of 1,3-Cycloalkanediols2006Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 71, nr 17, s. 6309-6316Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    An efficient desymmetrization of cis-1,3-cyclohexanediol to (1S,3R)-3-(acetoxy)-1-cyclohexanol ((R,S)-2a) was performed via Candida antarctica lipase B (CALB)-catalyzed transesterification, in high yield (up to 93%) and excellent enantioselectivity (ee's up to >99.5%). (R,R)-Diacetate ((R,R)-3a) was obtained in a DYKAT process at room temperature from (1S,3R)-3-acetoxy-1-cyclohexanol ((R,S)-2a), in a high trans/cis ratio (91:9) and in excellent enantioselectivity of >99%. Metal- and enzyme-catalyzed dynamic transformation of cis/trans-1,3-cyclohexanediol using PS-C gave a high diastereoselectivity for cis-diacetate (cis/trans = 97:3). The (1R,3S)-3-acetoxy-1-cyclohexanol (ent-(R,S)-2a) was obtained from cis-diacetate by CALB-catalyzed hydrolysis in an excellent yield (97%) and selectivity (>99% ee). By deuterium labeling it was shown that intramolecular acyl migration does not occur in the transformation of cis-monoacetate to the cis-diacetate.

  • 32. Fransson, Ann-Britt
    et al.
    Xu, Yongmei
    Leijondahl, Karin
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Enzymatic resolution, desymmetrization and dynamic kinetic asymmetric transformation of 1,3-cycloalkanediols2006Inngår i: Journal of organic chemistry, ISSN 0022-3263, Vol. 71, nr 17, s. 6309-6316Artikkel i tidsskrift (Fagfellevurdert)
  • 33.
    Gigant, Nicolas
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Access to Cinnamyl Derivatives from Arenes and Allyl Esters by a Biomimetic Aerobic Oxidative Dehydrogenative Coupling2014Inngår i: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 16, nr 6, s. 1664-1667Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    An efficient biomimetic aerobic oxidative dehydrogenative alkenylation of arenes with allyl esters is presented. The reaction proceeds under an ambient pressure of oxygen with relatively low catalyst loading of palladium acetate, employing catalytic amounts of electron-transfer mediators (ETMs). This study represents a new environmentally friendly method for the synthesis of cinnamyl derivatives.

  • 34.
    Gigant, Nicolas
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Aerobic Direct C-H Arylation of Nonbiased Olefins2014Inngår i: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 16, nr 17, s. 4432-4435Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    An efficient ligand-promoted biomimetic aerobic oxidative dehydrogenative cross-coupling between arenes and nonbiased olefins is presented. Acridine as a ligand was found to significantly enhance the rate, the yield, and the scope of the reaction under ambient oxygen pressure, providing a variety of alkenylarenes via an environmentally friendly procedure.

  • 35.
    Gigant, Nicolas
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Aerobic Double Dehydrogenative Cross Coupling between Cyclic Saturated Ketones and Simple Arenes2014Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, nr 20, s. 5890-5894Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The synthesis of 3-aryl-2-cyclohexenones is a topic of current interest as they are not only privileged structures in bioactive molecules, but they are also relevant feedstocks for the synthesis of substituted phenols or anilines, which are ubiquitous structural elements both in drug design and medicinal chemistry. A simple and sustainable one-pot aerobic double dehydrogenative reaction under mild conditions for the introduction of arenes in the -position of cyclic ketones has been developed. Starting from the corresponding saturated ketone, this reaction sequence proceeds under relatively low Pd catalyst loading and involves catalytic amounts of electron-transfer mediators (ETMs) under ambient oxygen pressure.

  • 36.
    Gustafson, Karl P. J.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Guðmundsson, Arnar
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bajnóczi, Éva
    Ning, Yuan
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för material- och miljökemi (MMK).
    Persson, Ingmar
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    In-Situ Structure Determination of a Ruthenium Racemization Catalyst and its Activated Intermediates using X-ray Absorption SpectroscopyManuskript (preprint) (Annet vitenskapelig)
  • 37.
    Gustafson, Karl P. J.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Görbe, Tamás
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    de Gonzalo Calvo, Gonzalo
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Yuan, Ning
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för material- och miljökemi (MMK).
    Schreiber, Cynthia
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Shchukarev, Andrey
    Tai, Cheuk-Wai
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för material- och miljökemi (MMK).
    Persson, Ingmar
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Application and further structure elucidation of Pd(0)-CalB CLEA biohybrid catalyst- Chemoenzymatic dynamic kinetic resolution of primary benzylic aminesManuskript (preprint) (Annet vitenskapelig)
  • 38.
    Gustafson, Karl P. J.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Lihammar, Richard
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Verho, Oscar
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Engström, Karin
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Chemoenzymatic Dynamic Kinetic Resolution of Primary Amines Using a Recyclable Palladium Nanoparticle Catalyst Together with Lipases2014Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 79, nr 9, s. 3747-3751Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A catalyst consisting of palladium nanoparticles supported on amino-functionalized siliceous mesocellular foam (Pd-AmP-MCF) was used in chemoenzymatic dynamic kinetic resolution (DKR) to convert primary amines to amides in high yields and excellent ee's. The efficiency of the nanocatalyst at temperatures below 70 degrees C enables reaction conditions that are more suitable for enzymes. In the present study, this is exemplified by subjecting 1-phenylethylamine (1a) and analogous benzylic amines to DKR reactions using two commercially available lipases, Novozyme-435 (Candida antartica Lipase B) and Amano Lipase PS-C1 (lipase from Burkholderia cepacia) as biocatalysts. The latter enzyme has not previously been used in the DKR of amines because of its low stability at temperatures over 60 degrees C. The viability of the heterogeneous Pd-AmP-MCF was further demonstrated in a recycling study, which shows that the catalyst can be reused up to five times.

  • 39.
    Gustafson, Karl P. J.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Shatskiy, Andrey
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Verho, Oscar
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kärkäs, Markus D.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Schluschass, Bastian
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tai, Cheuk-Wai
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för material- och miljökemi (MMK).
    Åkermark, Björn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Johnston, Eric V.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Water oxidation mediated by ruthenium oxide nanoparticles supported on siliceous mesocellular foam2017Inngår i: Catalysis Science & Technology, ISSN 2044-4753, E-ISSN 2044-4761, Vol. 7, nr 1, s. 293-299Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Artificial photosynthesis is an attractive strategy for converting solar energy into fuel. In this context, development of catalysts for oxidation of water to molecular oxygen remains a critical bottleneck. Herein, we describe the preparation of a well-defined nanostructured RuO2 catalyst, which is able to carry out the oxidation of water both chemically and photochemically. The developed heterogeneous RuO2 nanocatalyst was found to be highly active, exceeding the performance of most known heterogeneous water oxidation catalysts when driven by chemical or photogenerated oxidants.

  • 40.
    Guðmundsson, Arnar
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Gustafson, Karl P. J.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Khanh Mai, Binh
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Hobiger, Viola
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Yang, Bin
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Himo, Fahmi
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Iron Catalyzed Cyclization of N-protected a-Allenic Amines to 2,3-dihydropyrrolesManuskript (preprint) (Annet vitenskapelig)
  • 41.
    Görbe, Tamás
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Löfgren, Johanna
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Oschmann, Michael
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    S. Humble, Maria
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Transesterification of tert-Alcohols by Engineered Candida antarctica Lipase AManuskript (preprint) (Annet vitenskapelig)
  • 42.
    Hoben, Christine E.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kanupp, Lisa
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Practical chemoenzymatic dynamic kinetic resolution of primary amines via transfer of a readily removable benzyloxycarbonyl group2008Inngår i: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 49, nr 6, s. 977-979Artikkel i tidsskrift (Fagfellevurdert)
  • 43.
    Horváth, Attila
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Mild and Efficient Palladium(II)-Catalyzed Racemization of Allenes2004Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, nr 8, s. 964-965Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Allenes undergo racemization in the presence of catalytic amounts of Pd(OAc)2/LiBr under mild conditions; the reaction proceeds via a bromopalladation–debromopalladation sequence and tolerates various functional groups.

     

  • 44.
    Horváth, Attila
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Palladium(II)-Catalyzed SN2' Reactions of α-Allenic Acetates: Stereoconvergent Synthesis of (Z,E)-2-Bromo-1,3-dienes2001Inngår i: Journal of Organic Chemistry, Vol. 66, nr 24, s. 8120-8126Artikkel i tidsskrift (Fagfellevurdert)
  • 45.
    Horváth, Attila
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Benner, Jessica
    Simple, Enantiocontrolled Synthesis of 3-Pyrrolines from α-Amino Allenes2004Inngår i: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2004, nr 15, s. 3240-3243Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Cyclization of -amino allenes in the presence of N-bromosuccinimide afforded pyrrolines in good yields. The products were obtained with high enantiomeric excesses when optically active allenes were used as substrates. The synthesis of a 2,5-dehydroprolinol derivative is also presented.

  • 46.
    Horváth, Attila
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Jonasson, Catrin
    Bäckvall, Jan-Erling
    Intramolecular Palladium(II)-Catalyzed 1,2-Addition to Allenes2000Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, Vol. 122, nr 40, s. 9600-9609Artikkel i tidsskrift (Fagfellevurdert)
  • 47. Johansson, Mikael
    et al.
    Lindén, Auri
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Osmium-Catalyzed Dihydroxylaition of Alkenes by H2O2 in Room Temperature Ionic Liquid co-Catalyzed by VO(acac)2 or MeReO32005Inngår i: Journal of Organometallic Chemistry, ISSN 0022-328X, Vol. 690, nr 15, s. 3614-3619Artikkel i tidsskrift (Fagfellevurdert)
  • 48.
    Johnston, Eric V
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bogár, Krisztián
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Enantioselective synthesis of (R)-bufuralol via dynamic kinetic resolution in the key step2010Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 75, nr 13, s. 4596-4599Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    An enantioselective synthesis of (R)-bufuralol via a ruthenium- and enzyme-catalyzed dynamic kinetic resolution (DKR) has been achieved. The synthesis starts from readily available 2-ethylphenol and provides (R)-bufuralol in high ee and a good overall yield of 31%.

  • 49.
    Johnston, Eric V.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Oxidation of carbonyl compounds2010Inngår i: Modern Oxidation Methods / [ed] Jan-Erling Bäckvall, Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA , 2010, 2, s. 353-369Kapittel i bok, del av antologi (Annet vitenskapelig)
  • 50.
    Kadow, Maria
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Ernst Moritz Arndt Universitat Greifswald, Germany.
    Balke, Kathleen
    Willetts, Andrew
    Bornscheuer, Uwe T.
    Bäckvall, Jan-Erling
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Functional assembly of camphor converting two-component Baeyer-Villiger monooxygenases with a flavin reductase from E-coli2014Inngår i: Applied Microbiology and Biotechnology, ISSN 0175-7598, E-ISSN 1432-0614, Vol. 98, nr 9, s. 3975-3986Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The major limitation in the synthetic application of two-component Baeyer-Villiger monooxygenases was addressed by identifying the 28-kDa flavin-reductase Fre from Escherichia coli as a suitable supplier of reduced FMN for these enzymes. Coexpression of Fre with either 2,5- or 3,6-diketocamphane monooxygenase from Pseudomonas putida NCIMB 10007 significantly enhanced the conversion of camphor and norcamphor serving as representative ketones. With purified enzymes, full conversion was achieved, while only slight amounts of product were formed in the absence of this flavin reductase. Fusion of the genes of Fre and DKCMOs into single open reading frame constructs resulted in unstable proteins exhibiting flavin reducing, but poor oxygenating activity, which led to overall decreased conversion of camphor.

123 1 - 50 of 111
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