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CBS reduction

The CBS reduction, in full the Corey-Bakshi-Shibata reduction, is an organic reaction which transforms ketones enantioselectively into alcohols.^[1]^[2]^[3] This is done by using the so-called CBS catalyst, a bicyclic boron-containing proline derivative, along with diborane as the hydrogen donor.^[4]^[5]^[6]

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The oxazaborolidine reagent which mediates the enantioselective reduction was previously developed by the laboratory of Itsuno,^[7] and thus this transformation may more properly be called the Itsuno-Corey oxazaborolidine reduction.

References

^ Corey, E. J.; Shibata, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861-2863.
^ Organic Syntheses, Coll. Vol. 9, p.676 (1998); Vol. 74, p.50 (1997) (Article)
^ Organic Syntheses, Coll. Vol. 9, p.362 (1998); Vol. 74, p.33 (1997) (Article).
^ Mechanistic Aspects of the CBS reduction
^ Evans, M. A.; Morken, J. P. Org. Lett. 2005, 7, 3371-3373.
^ For examples see Organic Syntheses, Coll. Vol. 10, p.448 (2004); Vol. 79, p.72 (2002) (Article)
^ Itsuno, S.; Ito, K.; Hirao, A.; Nakahama, S. J. Chem. Soc., Chem. Commun. 1983, 8, 469.