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Catalytic Asymmetric Staudinger–aza-Wittig Reaction for the Synthesis of Heterocyclic Amines

  • Lingchao Cai
    Lingchao Cai
    Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States
    More by Lingchao Cai
  • Kui Zhang
    Kui Zhang
    Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States
    More by Kui Zhang
  • Shuming Chen
    Shuming Chen
    Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States
    More by Shuming Chen
  • Romain J. Lepage
    Romain J. Lepage
    School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Queensland 4072, Australia
  • K. N. Houk
    K. N. Houk
    Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States
    More by K. N. Houk
  • Elizabeth H. Krenske
    Elizabeth H. Krenske
    School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Queensland 4072, Australia
  • , and 
  • Ohyun Kwon*
    Ohyun Kwon
    Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States
    *[email protected]
    More by Ohyun Kwon
Cite this: J. Am. Chem. Soc. 2019, 141, 24, 9537–9542
Publication Date (Web):June 4, 2019
https://doi.org/10.1021/jacs.9b04803
Copyright © 2019 American Chemical Society

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    Abstract

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    Many natural products and medicinal drugs are heterocyclic amines possessing a chiral quaternary carbon atom in their heterocyclic ring. Herein, we report the first catalytic and asymmetric Staudinger–aza-Wittig reaction for the desymmetrization of ketones. This highly enantioselective transformation proceeds at room temperature to provide high yields—even on multigram scales—of nitrogen heterocycles featuring a chiral quaternary center. The products of this reaction are potential precursors for the synthesis of pharmaceuticals. A commercially available small P-chiral phosphine catalyst, HypPhos, induces the asymmetry and is recycled through in situ reduction of its oxide, mediated by phenylsilane in the presence of a carboxylic acid. The efficiency, selectivity, scalability, mild reaction conditions, and broad substrate scope portend that this process will expedite the syntheses of chiral heterocyclic amines of significance to chemistry, biology, and medicine.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.9b04803.

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