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Enzymatic kinetic resolution of sec-alcohols using an ionic liquid anhydride as acylating agent
Affiliation:1. Department of Materials Science and Engineering, National Defense Academy, 1-10-20 Hashirimizu, Yokosuka 239-8686, Japan;2. Department of Applied Chemistry, National Defense Academy, 1-10-20 Hashirimizu, Yokosuka 239-8686, Japan;3. Graduate School of Humanities and Sciences, Ochanomizu University, 2-1-1 Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan
Abstract:A task-specific ionic liquid bearing an anhydride moiety was synthesized for the first time in good yield (83%) through a carbodiimide-mediated coupling reaction. The enantiomeric separation of a series of sec-alcohols was performed via enzymatic kinetic resolution, employing an ionic anhydride as acylating agent and Candida antarctica Lipase B as a biocatalyst. A fast and efficient recovery of both enantiomers was achieved separately due to the ionic nature of the acyl donor, combined with the possibility of carrying out the enzymatic step in an organic solvent.
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