Enzymatic kinetic resolution of racemic cyanohydrins via enantioselective acylation |
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| Authors: | Qing Xu Xiaohong Geng |
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| Affiliation: | a College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 Renmin Road North, Songjiang District, Shanghai 201620, China
b State Key Laboratory of Bioorganic Chemistry and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Fenglin Road, Shanghai 200032, China |
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| Abstract: | Enzymatic kinetic resolution of a series of aromatic and aliphatic cyanohydrins in organic media has been investigated. The behavior of potential lipases, molecular sieves, acyl reagent, reaction temperature, and organic solvents on the kinetic resolution was studied. The influence of substrate structure, steric, and electronic nature and position of the aryl substituent on the enantioselectivity was discussed. Under the optimized reaction conditions, good enantioselectivity could be achieved for most of the investigated compounds. Specifically, substrates 1a, 1c, 1d, 1f, 1u could be resolved with the kinetic enantiomer ratio (E) higher than 200. |
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| Keywords: | Enzymatic kinetic resolution Cyanohydrin Enantioselective acylation Lipase |
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