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Practical enantioselective reduction of ketones using oxazaborolidine catalyst generated in situ from chiral lactam alcohol and borane

Yasuhiro Kawanami*, Shinichi Murao, Takahiko Ohga and Nobuyo Kobayashi

*Department of Biochemistry and Food Science, Faculty of Agriculture, Kagawa University, Miki-cho, Kagawa 761-0795, Japan, Email:

Y. Kawanami, S. Murao, T. Ohga, N. Kobayashi, Tetrahedron, 2003, 59, 8411-8414.

DOI: 10.1016/j.tet.2003.08.064


A chiral oxazaborolidine catalyst prepared in situ from a chiral lactame and borane at room temperature catalyzed the enantioselective reduction of ketones with high enantioselectivity. The preparation of the catalyst is not time consuming and no expensive reagents are involved.

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Possible pathway to the oxazaborolidine

Key Words

Corey-Bakshi-Shibata Reduction, CBS Reduction, borane, asymmetric synthesis, enantioselective, lactam alcohol

ID: J72-Y2003-850