Lipase-Catalyzed Kinetic Resolution on Solid-Phase via a "Capture and Release" Strategy

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The lipase-catalyzed kinetic resolution of (R/S)-3-phenylbutyric acid 2 using solid-supported cyclohexane-1,3-dione (CHD) 6 is described. In each case the predominant enantiomer observed, after cleavage from the resin, was (R)-(?)-3-phenylbutyric acid (R)-2 (ee > 99%) rather than the expected (S)-enantiomer of 2. This observation is in contrast to the fact that Chromobacterium viscosum lipase shows high enantiospecificity for the (S)-enantiomer in the corresponding solution-phase hydrolysis reactions. The (R)-acyl group was subsequently released from the resin by NaOH hydrolysis, and the yield of the reaction could be improved by triple acylation of the resin. Copyright © 2003 American Chemical Society.

Bibliographical metadata

Original languageEnglish
Pages (from-to)13952-13953
Number of pages1
JournalJournal of the American Chemical Society
Issue number46
Publication statusPublished - 19 Nov 2003