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    Ring-Contraction Strategy for the Practical, Scalable, Catalytic Asymmetric Synthesis of Versatile γ-Quaternary Acylcyclopentenes

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    Type
    Article
    Authors
    Hong, Allen Y.
    Krout, Michael R.
    Jensen, Thomas
    Bennett, Nathan B.
    Harned, Andrew M.
    Stoltz, Brian M.
    KAUST Grant Number
    KUS-11-006-02
    Date
    2011-02-24
    Online Publication Date
    2011-02-24
    Print Publication Date
    2011-03-14
    Permanent link to this record
    http://hdl.handle.net/10754/599515
    
    Metadata
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    Abstract
    Contraction action! A simple protocol for the catalytic asymmetric synthesis of highly functionalized γ-quaternary acylcyclopentenes (see schematic) in up to 91 % overall yield and 92 % ee has been developed. The reaction sequence employs a palladium-catalyzed enantioselective alkylation reaction and exploits the unusual stability of β-hydroxy cycloheptanones to achieve a general and robust method for performing two-carbon ring contractions.
    Citation
    Hong AY, Krout MR, Jensen T, Bennett NB, Harned AM, et al. (2011) Ring-Contraction Strategy for the Practical, Scalable, Catalytic Asymmetric Synthesis of Versatile γ-Quaternary Acylcyclopentenes. Angew Chem 123: 2808–2812. Available: http://dx.doi.org/10.1002/ange.201007814.
    Sponsors
    This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). The authors wish to thank NIH-NIGMS (R01M080269-01), Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. M.R.K. acknowledges Eli Lilly for a predoctoral fellowship. T.J. acknowledges the Danish Council for Independent Research/Natural Sciences for a postdoctoral fellowship. Materia, Inc. is gratefully acknowledged for the donation of catalysts. Lawrence Henling and Dr. Michael Day are gratefully acknowledged for X-ray crystallographic structure determination. The Bruker KAPPA APEXII X-ray diffractometer used in this study was purchased via an NSF CRIF:MU award to Caltech (CHE-0639094). Prof. Sarah Reisman, Dr. Scott Virgil, Dr. Christopher Henry, and Nathaniel Sherden are acknowledged for helpful discussions. Dr. David VanderVelde and Dr. Scott Ross are acknowledged for NMR assistance. The Varian 400 MR instrument used in this study was purchased via an NIH award to Caltech (NIH RR027690). Dr. Mona Shahgholi and Naseem Torian are acknowledged for high-resolution mass spectrometry assistance.
    Publisher
    Wiley
    Journal
    Angewandte Chemie
    DOI
    10.1002/ange.201007814
    ae974a485f413a2113503eed53cd6c53
    10.1002/ange.201007814
    Scopus Count
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