Journal of Oleo Science
Online ISSN : 1347-3352
Print ISSN : 1345-8957
ISSN-L : 1345-8957
Chemistry and Organic Synthesis
Combination of Novozym 435-catalyzed Enantioselective Hydrolysis and Amidation for the Preparation of Optically Active δ-Hexadecalactone
Yasutaka ShimotoriMasayuki HoshiTetsuo Miyakoshi
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2015 Volume 64 Issue 5 Pages 561-575

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Abstract

A new enzymatic method for synthesis of enantiomerically enriched δ-hexadecalactone (3) based on the enzymatic kinetic resolution of N-methyl-5-acetoxyhexadecanamide (1) is described. A combination of lipase-catalyzed hydrolysis and amidation improved enantioselectivity. Lipase-catalyzed amidation was also investigated. Detailed screening of solvents and additive amines was performed. The addition of cyclohexylamine to lipase-catalyzed hydrolysis afforded the best results to give both enantiomers of 3 with more than 90% enantiomeric excess.

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© 2015 by Japan Oil Chemists' Society
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