Core-Structure-Motivated Design of Iminium–Enolate Organocascade Reactions: Enantioselective Syntheses of 5,6-Dihydroindolizines

Authors

  • Dr. Xianxing Jiang,

    1. The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Cell and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
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  • Bin Tan,

    1. The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Cell and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
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  • Prof. Dr. Carlos F. Barbas III

    Corresponding author
    1. The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Cell and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    • The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Cell and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)

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  • Research support from the Skaggs Institute for Chemical Biology is gratefully acknowledged. We thank Prof. C. E. Moore for X-ray crystallographic analysis (Department of Chemistry and Biochemistry, University of San Diego) and Klaus Albertshofer and Jia Liu for assistance.

Abstract

original image

Indolizine skeletons: A highly efficient dual iminium–enolate generation/activation process is introduced as a new platform for the design of organocatalytic intermolecular domino reactions for the direct construction of 5,6-dihydroindolizine derivatives. This process provides ready access to indolizine skeletons with high optically purity from simple starting materials (see picture).

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