Lipase-catalyzed kinetic resolution on solid-phase via a "capture and release" strategy

Humphrey, C E and Turner, N J and Easson, M A M and Flitsch, S L and Ulijn, R V (2003) Lipase-catalyzed kinetic resolution on solid-phase via a "capture and release" strategy. Journal of the American Chemical Society, 125 (46). pp. 13952-13953. ISSN 0002-7863

Full text not available in this repository.Request a copy from the Strathclyde author

Abstract

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.