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Rationally Designed Amide Donors for Organocatalytic Asymmetric Michael Reactions

Authors

  • Dr. Bin Tan,

    1. The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
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  • Dr. Gloria Hernández-Torres,

    1. The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)
    2. Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain)
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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 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 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 also thank Dr. A. L. Rheingold and Dr. C. E. Moore for the X-ray crystallographic analysis. G.H.-T. also thanks Universidad Autónoma de Madrid for financial support.

Abstract

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Amide nucleophiles on demand: Rationally designed pyrazoleamides function as Michael donors in urea-catalyzed asymmetric Michael reactions with excellent chemical and optical yields (see scheme). The pyrazoleamide group performs as an ester equivalent, a directing group, an activating group, and functions as a good leaving group in further transformations of the product.

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