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    Enantioselective construction of quaternary N-heterocycles by palladium-catalysed decarboxylative allylic alkylation of lactams

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    Type
    Article
    Authors
    Behenna, Douglas C.
    Liu, Yiyang
    Yurino, Taiga
    Kim, Jimin
    White, David E.
    Virgil, Scott C.
    Stoltz, Brian M.
    KAUST Grant Number
    KUS-11-006-02
    Date
    2011-12-18
    Online Publication Date
    2011-12-18
    Print Publication Date
    2012-02
    Permanent link to this record
    http://hdl.handle.net/10754/598160
    
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    Abstract
    The enantioselective synthesis of nitrogen-containing heterocycles (N-heterocycles) represents a substantial chemical research effort and resonates across numerous disciplines, including the total synthesis of natural products and medicinal chemistry. In this Article, we describe the highly enantioselective palladium-catalysed decarboxylative allylic alkylation of readily available lactams to form 3,3-disubstituted pyrrolidinones, piperidinones, caprolactams and structurally related lactams. Given the prevalence of quaternary N-heterocycles in biologically active alkaloids and pharmaceutical agents, we envisage that our method will provide a synthetic entry into the de novo asymmetric synthesis of such structures. As an entry for these investigations we demonstrate how the described catalysis affords enantiopure quaternary lactams that intercept synthetic intermediates previously used in the synthesis of the Aspidosperma alkaloids quebrachamine and rhazinilam, but that were previously only available by chiral auxiliary approaches or as racemic mixtures. © 2012 Macmillan Publishers Limited. All rights reserved.
    Citation
    Behenna DC, Liu Y, Yurino T, Kim J, White DE, et al. (2011) Enantioselective construction of quaternary N-heterocycles by palladium-catalysed decarboxylative allylic alkylation of lactams. Nature Chem 4: 130–133. Available: http://dx.doi.org/10.1038/NCHEM.1222.
    Sponsors
    This publication is based on work supported by award from the King Abdullah University of Science and Technology (KAUST; no. KUS-11-006-02). The authors thank NIH-NIGMS (R01GM080269-01 and a postdoctoral fellowship to D.E.W.), the Gordon and Betty Moore Foundation, Amgen, Abbott, Boehringer Ingelheim and Caltech for financial support. T.Y. acknowledges the Japan Society for the Promotion of Science for a predoctoral fellowship.
    Publisher
    Springer Nature
    Journal
    Nature Chemistry
    DOI
    10.1038/NCHEM.1222
    PubMed ID
    22270628
    ae974a485f413a2113503eed53cd6c53
    10.1038/NCHEM.1222
    Scopus Count
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    Publications Acknowledging KAUST Support

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