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Asymmetric Baeyer-Villiger Reaction with Hydrogen Peroxide Catalyzed by a Novel Planar-Chiral Bisflavin

Shun-Ichi Murahashi*, Satoshi Ono, Yasushi Imada

*Department of Applied Chemistry, Faculty of Engineering, Okayama University of Science, 1-1, Ridaicho, Okayama 700-0005 (Japan), Email:murahashihigh.ous.ac.jp

S. Murahashi, S. Ono, Y. Imada, Angew. Chem. Int. Ed., 2002, 41, 2366-2368.

DOI: 10.1002/1521-3773(20020703)41:13<2366::AID-ANIE2366>3.0.CO;2-S


Abstract

The synthesis of a planar-chiral bisflavin catalyst (1) and its use in asymmetric Bayer-Villiger-Oxidations is described. 

R Yield ee [%]
4-MeOC6H4 67 61 (+)
Ph 67 63 (S)
4-BrC6H4 28 68 (+)

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Key Words

Baeyer-Villiger Oxidation, asymmetric catalysis, biomimetic synthesis, enantioselectivity, lactones, oxidation, hydrogen peroxide, organocatalysis


ID: J06-Y2002-970