Oxazaborolidines as functional monomers: ketone reduction using polymer-supported Corey, Bakshi, and Shibata catalysts.

Abstract

The first two polymer-supported versions of the Corey, Bakshi, and Shibata (CBS) catalyst have been prepared. Functional monomers based structurally upon the original B-methylated catalyst have been used to prepare catalytic polymers containing the CBS moiety bound both in a pendant fashion and in the form of a cross-link. Enantioselective reductions of two prochiral ketones have been carried out using the original catalyst in the solution phase as well as the two solid-state systems. While the pendant-bound system shows reduced stereoselectivity, the cross-linked version affords enantioselectivities almost identical to those of the solution-phase model.