Double Asymmetric Synthesis and a New Strategy for Stereochemical Control in Organic Synthesis

Authors

  • Prof. Dr. Satoru Masamune,

    Corresponding author
    1. Department of Chemistry, Massachusetts Institute of Technology Cambridge, MA 02 139 (USA)
    • Department of Chemistry, Massachusetts Institute of Technology Cambridge, MA 02 139 (USA)
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  • Dr. William Choy,

    1. Department of Chemistry, Massachusetts Institute of Technology Cambridge, MA 02 139 (USA)
    Current affiliation:
    1. Department of Chemistry, University of Denver, Denver, CO 80208 (USA)
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  • Dr. John S. Petersen,

    1. Department of Chemistry, Massachusetts Institute of Technology Cambridge, MA 02 139 (USA)
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  • Lawrence R. Sita

    1. Department of Chemistry, Massachusetts Institute of Technology Cambridge, MA 02 139 (USA)
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  • Dedicated to Professor Raymond U. Lemieux on the occasion of his 65th birthday

Abstract

This account examines double asymmetric induction from theoretical and practical viewpoints. In the context of four major organic reactions-the aldol, Diels-Alder, catalytic hydrogenation, and epoxidation-it is shown that a double asymmetric induction can be analyzed in terms of the single asymmetric reactions of each of the two chiral reactants. A rule which qualitatively relates the results of these single asymmetric reactions with the outcome of the double asymmetric reaction is proposed. A powerful new strategy based on this rule for the predictable creation of new chiral centers is discussed and the use of this strategy for the synthesis of sugars and macrolides is presented.

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