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DOI: 10.1055/s-2007-991332
Enzymatic Resolution on Ionic Acylating Agents
N. M. T. Lourenço, C. A. M. Afonso*
Instituto Superior Técnico, Lisboa and Universidade Nova de Lisboa, Caparica, Portugal
Publication History
Publication Date:
22 November 2007 (online)
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Significance
A one-pot process for the resolution and separation of both enantiomers of sec-alcohols rac-1 via two consecutive enzymatic transesterifications with lipase B from Candida antarctica 2 (CALB) is reported. The separation is based on the temporal attachment of one of the enantiomers (R)-1 to imidazolium ionic acylating agent 3 in ionic liquid 4 ([bmim][PF6]). Due to this attachment by enantioselective transesterification, the free enantiomer (S)-1 can be isolated by simple extraction with organic solvents. Subsequently, a second transesterification with ethanol releases the attached enantiomer (R)-1 and regenerates the reaction mixture of enzyme 2, ionic acylating agent 3, and ionic liquid 4 for reuse.