Corey-Itsuno Reduction

The Corey-Itsuno Reduction, also known as the Corey-Bakshi-Shibata (CBS) reduction, is a chemical reaction in which an achiral ketone is enantioselectively reduced to produce the corresponding chiral, non-racemic alcohol. The oxazaborolidine reagent which mediates the enantioselective reduction of ketones was previously developed by the laboratory of Itsuno and thus this transformation may more properly be called the Itsuno-Corey oxazaborolidine reduction.

In 1981, Itsuno and coworkers first reported the use of chiral alkoxy-amine-borane complexes in reducing achiral ketones to chiral alcohols enantioselectively and in high yield. Several years later in 1987, E. J. Corey and coworkers developed the reaction between chiral amino alcohols and borane (BH3), generating oxazaborolidine products which were shown to rapidly catalyze the enantioselective reduction of achiral ketones in the presence of BH3•THF.

The CBS Reduction has since been utilized by organic chemists as a reliable method for the asymmetric reduction of achiral ketones. Notably, it has found prominent use not only in a number of natural product syntheses, but has been utilized on large scale in industry (See Scope Below). Several reviews have been published.

Read more about Corey-Itsuno Reduction:  Mechanism, Variations, Applications

Other articles related to "reduction":

Corey-Itsuno Reduction - Applications
... Over the past couple of decades, the CBS Reduction has gained significant synthetic utility in the synthesis of a significant number of natural products, including ... The enantionselective reduction has also been employed on large scale in industry ... utilized the CBS reduction in the total synthesis of MK-0417, a water-soluble carbonic anhydrase inhibitor which has been used therapeutically to reduce intraocular pressure ...

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