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 proton donor.
[4][5][6]
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
1. Corey, E. J.; Shibata, S.; Bakshi, R. K. ''J. Org. Chem.'' '1988', ''53'', 2861-2863.
2. ''Organic Syntheses'', Coll. Vol. 9, p.676 (1998); Vol. 74, p.50 (1997) (Article)
3. Organic Syntheses, Coll. Vol. 9, p.362 (1998); Vol. 74, p.33 (1997) (Article).
4. Mechanistic Aspects of the CBS reduction
5. Evans, M. A.; Morken, J. P. ''Org. Lett.'' '2005', ''7'', 3371-3373.
6. For examples see ''Organic Syntheses'', Coll. Vol. 10, p.448 (2004); Vol. 79, p.72 (2002) (Article)
7. Itsuno, S.; Ito, K.; Hirao, A.; Nakahama, S. ''J. Chem. Soc., Chem. Commun.'' '1983', ''8'', 469.