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Corey-Bakshi-Shibata Reduction Itsuno-Corey Reduction

Lianyungang Klinechem Co.,Ltd | Updated: Dec 11, 2018

Corey-Bakshi-Shibata Reduction
Itsuno-Corey Reduction

The enantioselective reduction of ketones using borane and a chiral oxazaborolidine as catalyst (CBS catalyst). Usually, MeCBS is used (R'' = Me, but selectivity may be increased by varying this substituent).

Mechanism of the Corey-Bakshi-Shibata Reduction

The mechanism depicted (E. J. Corey, C. J. Helal, Angew. Chem. Int. Ed.199837, 1986-2012. DOI) portrays the rationale for the enantioselectivity and high reaction rates, which are influenced only by the CBS catalyst. This catalyst is a combination of both a Lewis acid and a chiral auxiliary!

Recent Literature

Practical enantioselective reduction of ketones using oxazaborolidine catalyst generated in situ from chiral lactam alcohol and borane
Y. Kawanami, S. Murao, T. Ohga, N. Kobayashi, Tetrahedron200359, 8411-8414.

An Efficient and Catalytically Enantioselective Route to (S)-(-)-Phenyloxirane
E. J. Corey, S. Shibata, R. K. Bakshi, J. Org, Chem.198853, 2861-2863.

A novel enantioselective synthesis of α-amino acids has been developed, which is broad in scope, simple in application, and advantageous for many α-amino acids of interest in chemistry, biology, medicine.
E. J. Corey, J. O. Link, J. Am. Chem. Soc.1992114, 1906-1908.

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