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

Michael D. Price, Jennifer K. Sui, Mark J. Kurth, Neil E. Schore

Research output: Contribution to journalArticle

44 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)8086-8089
Number of pages4
JournalJournal of Organic Chemistry
Volume67
Issue number23
DOIs
StatePublished - Nov 15 2002

ASJC Scopus subject areas

  • Organic Chemistry

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