Journal of the American Chemical Society 2003-11-19

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

Cara E Humphrey, Nicholas J Turner, Morag A M Easson, Sabine L Flitsch, Rein V Ulijn

Index: J. Am. Chem. Soc. 125(46) , 13952-3, (2003)

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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.