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.
Original language | English |
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Pages (from-to) | 13952-13953 |
Number of pages | 2 |
Journal | Journal of the American Chemical Society |
Volume | 125 |
Issue number | 46 |
Early online date | 25 Oct 2003 |
DOIs | |
Publication status | Published - 19 Nov 2003 |
Keywords
- lipase-catalyzed kinetic resolution
- solid-phase
- capture and release strategy