Reduction of Carbonyl Compounds with Chiral Oxazaborolidine Catalysts: A New Paradigm for Enantioselective Catalysis and a Powerful New Synthetic Method

Elias J Corey; Christopher J Helal

doi:10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO;2-Z

Reduction of Carbonyl Compounds with Chiral Oxazaborolidine Catalysts: A New Paradigm for Enantioselective Catalysis and a Powerful New Synthetic Method

Angew Chem Int Ed Engl. 1998 Aug 17;37(15):1986-2012. doi: 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO;2-Z.

Authors

Elias J Corey¹, Christopher J Helal¹

Affiliation

¹ Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138 (USA), Fax: (+1) 617-495-0376.

Abstract

High enantioselectivity can be achieved when chiral oxazaborolidines are used as catalysts in the reduction of ketones by borane. In the transition state on the way to the complex chiral compounds, the two reactants are activated and held in close proximity by the catalyst, as shown below.

Keywords: Asymmetric catalysis; Boron; Ketones; Reductions; Total synthesis.

Publication types

Review