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Multifunctional asymmetric catalysis.

M Shibasaki1, M Kanai

  • 1Graduate School of Pharmaceutical Sciences, The University of Tokyo, Japan. mshibasa@mol.f.u-tokyo.ac.jp

Chemical & Pharmaceutical Bulletin
|June 1, 2001
PubMed
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New enantioselective catalysts were developed using bimetallic complexes and bifunctional Lewis acid-Lewis base catalysts for key organic reactions. These catalysts achieved high enantioselectivity in nitro-Mannich, aldol reactions, and cyanosilylation, enabling complex molecule synthesis.

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Asymmetric Synthesis

Background:

  • Development of enantioselective catalysts is crucial for synthesizing chiral molecules.
  • Multifunctional catalysis offers a promising strategy for designing efficient catalytic systems.
  • Existing methods often lack the desired selectivity or scope for complex transformations.

Purpose of the Study:

  • To develop novel general and practical enantioselective catalysts based on multifunctional catalysis.
  • To explore the application of these catalysts in key carbon-carbon bond-forming reactions.
  • To demonstrate the utility of these catalysts in the synthesis of complex natural products.

Main Methods:

  • Design and synthesis of bimetallic complexes (e.g., Ytterbium-Potassium-BINOL) for enantioselective reactions.

Related Experiment Videos

  • Development of Lewis acid-Lewis base bifunctional catalysts for nucleophilic additions.
  • Application of developed catalysts in enantioselective nitro-Mannich, aldol reactions, and cyanosilylation.

    • Main Results:

    • Bimetallic complexes achieved up to 91% ee in the nitro-Mannich reaction and high enantioselectivity in aldol reactions.
    • Second-generation ALB catalysts provided high enantioselectivity (up to 83% ee) and diastereoselectivity (up to 7:1) in nitro-Mannich reactions.
    • Lewis acid-Lewis base catalysts enabled highly enantioselective cyanation of electrophiles and were applied to epothilone synthesis.

    Conclusions:

    • The developed bimetallic and bifunctional Lewis acid-Lewis base catalysts represent a significant advancement in enantioselective catalysis.
    • These catalysts demonstrate broad applicability in various organic transformations, including those relevant to natural product synthesis.
    • Multifunctional catalysis provides a powerful platform for creating efficient and selective catalytic systems.