CBS reduction

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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]

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.

CBS reduction of a ketone, where R1 is a larger group than R2.
CBS reduction of a ketone, where R1 is a larger group than R2.

[edit] 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.
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