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  • 1.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ahlsten, Nanna
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martin-Matute, Belen
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enantioselective Synthesis of Alcohols and Amines by Iridium-Catalyzed Hydrogenation, Transfer Hydrogenation, and Related Processes2013In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 19, no 23, p. 7274-7302Article, review/survey (Refereed)
    Abstract [en]

    The preparation of chiral alcohols and amines by using iridium catalysis is reviewed. The methods presented include the reduction of ketones or imines by using hydrogen (hydrogenations), isopropanol, formic acid, or formate (transfer hydrogenations). Also dynamic and oxidative kinetic resolutions leading to chiral alcohols and amines are included. Selected literature reports from early contributions to December 2012 are discussed.

  • 2.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Marcos, Rocio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sahoo, Suman
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Inge, A. Ken
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A Highly Active Bifunctional Iridium Complex with an Alcohol/Alkoxide-Tethered N-Heterocyclic Carbene for Alkylation of Amines with Alcohols2012In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 45, p. 14510-14519Article, review/survey (Refereed)
    Abstract [en]

    A series of new iridium(III) complexes containing bidentate N-heterocyclic carbenes (NHC) functionalized with an alcohol or ether group (NHC?OR, R=H, Me) were prepared. The complexes catalyzed the alkylation of anilines with alcohols as latent electrophiles. In particular, biscationic IrIII complexes of the type [Cp*(NHC-OH)Ir(MeCN)]2+2[BF4-] afforded higher-order amine products with very high efficiency; up to >99?% yield using a 1:1 ratio of reactants and 12.5 mol?% of Ir, in short reaction times (216 h) and under base-free conditions. Quantitative yields were also obtained at 50?degrees C, although longer reaction times (4860 h) were needed. A large variety of aromatic amines have been alkylated with primary and secondary alcohols. The reactivity of structurally related iridium(III) complexes was also compared to obtain insights into the mechanism and into the structure of possible catalytic intermediates. The IrIII complexes were stable towards oxygen and moisture, and were characterized by NMR, HRMS, single-crystal X-ray diffraction, and elemental analyses.

  • 3.
    Lundberg, Helena
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tinnis, Fredrik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Selander, Nicklas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Catalytic amide formation from non-activated carboxylic acids and amines2014In: Chemical Society Reviews, ISSN 0306-0012, E-ISSN 1460-4744, Vol. 43, no 8, p. 2714-2742Article, review/survey (Refereed)
    Abstract [en]

    The amide functionality is found in a wide variety of biological and synthetic structures such as proteins, polymers, pesticides and pharmaceuticals. Due to the fact that synthetic amides are still mainly produced by the aid of coupling reagents with poor atom-economy, the direct catalytic formation of amides from carboxylic acids and amines has become a field of emerging importance. A general, efficient and selective catalytic method for this transformation would meet well with the increasing demands for green chemistry procedures. This review covers catalytic and synthetically relevant methods for direct condensation of carboxylic acids and amines. A comprehensive overview of homogeneous and heterogeneous catalytic methods is presented, covering biocatalysts, Lewis acid catalysts based on boron and metals as well an assortment of other types of catalysts.

  • 4.
    Marcos, Rocio
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Combined Enzyme and Transition-Metal Catalysis for Dynamic Kinetic Resolutions2012In: Israel Journal of Chemistry, ISSN 0021-2148, Vol. 52, no 7, p. 639-652Article, review/survey (Refereed)
    Abstract [en]

    The preparation of optically pure alcohols, axially chiral allenes, and amine derivatives by using enzymes and transition-metal catalysts through dynamic kinetic resolution (DKR) is reviewed. After a general introduction into enzymatic kinetic resolutions and racemizations catalyzed by transition-metal complexes, selected examples of DKRs are presented, from early work to more recent outstanding contributions, and also applications of this approach.

  • 5.
    Otero-Fraga, Jorge
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Montesinos-Magraner, Marc
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mendoza, Abraham
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Perspectives on Intermolecular Azomethine Ylide [3+2] Cycloadditions with Non-Electrophilic Olefins2017In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, Vol. 49, no 4, p. 802-809Article, review/survey (Refereed)
    Abstract [en]

    Our interest in the synthesis of compact nitrogen heterocycles from abundant sources has motivated a critical analysis of the status in azomethine ylide chemistry. Despite the outstanding developments in catalytic enantioselective [3+2] cycloadditions, these are still limited to electron-poor olefins. Only a few examples can be found in the literature that report on cycloadditions using non-electrophilic alkenes and those are compiled herein. With this account we aim to extract lessons and challenges that will inspire future breakthroughs in this area.

  • 6. Silva, Luiz F., Jr.
    et al.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hypervalent iodine reagents in the total synthesis of natural products2011In: Natural product reports (Print), ISSN 0265-0568, E-ISSN 1460-4752, Vol. 28, no 10, p. 1722-1754Article, review/survey (Refereed)
    Abstract [en]

    This report describes the recent applications of hypervalent iodine reagents in the total synthesis of natural products. The large diversity of high-yielding and chemoselective reactions that can be achieved, even for highly functionalized molecules, is summarized, demonstrating that hypervalent iodine reagents have become an essential tool in synthetic organic chemistry.

  • 7. Thorsheim, Karin
    et al.
    Siegbahn, Anna
    Johnsson, Richard E.
    Stalbrand, Henrik
    Manner, Sophie
    Bartholomeyzik, Teresa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ellervik, Ulf
    Chemistry of xylopyranosides2015In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 418, p. 65-88Article, review/survey (Refereed)
    Abstract [en]

    Xylose is one of the few monosaccharidic building blocks that are used by mammalian cells. In comparison with other monosaccharides, xylose is rather unusual and, so far, only found in two different mammalian structures, i.e. in the Notch receptor and as the linker between protein and glycosaminoglycan (GAG) chains in proteoglycans. Interestingly, simple soluble xylopyranosides can not only initiate the biosynthesis of soluble GAG chains but also function as inhibitors of important enzymes in the biosynthesis of proteoglycans. Furthermore, xylose is a major constituent of hemicellulosic xylans and thus one of the most abundant carbohydrates on Earth. Altogether, this has spurred a strong interest in xylose chemistry. The scope of this review is to describe synthesis of xylopyranosyl donors, as well as protective group chemistry, modifications, and conformational analysis of xylose.

  • 8. Verendel, J. Johan
    et al.
    Pamies, Oscar
    Dieguez, Montserrat
    Andersson, Pher G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Univ KwaZulu Natal, Sch Chem, Durban, South Africa.
    Asymmetric Hydrogenation of Olefins Using Chiral Crabtree-type Catalysts: Scope and Limitations2014In: Chemical Reviews, ISSN 0009-2665, E-ISSN 1520-6890, Vol. 114, no 4, p. 2130-2169Article, review/survey (Refereed)
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