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Paper | Regular issue | Vol 85, No. 5, 2012, pp.1061-1075
Published online, 30th March, 2012
DOI: 10.3987/COM-12-12426
Enantioselective Synthesis of ε-Lactones by Lipase-Catalyzed Resolution

Yasutaka Shimotori,* Masakazu Aoyama, Hidetaka Tsukasa, and Tetsuo Miyakoshi

*Department of Biotechnology and Environmental Chemistry, Kitami Institute of Technology, Koen-cho 165, Kitami, Hokkaido 090-8507, Japan

Abstract

Synthesis of optically active ε-dodecalactone (1) by lipase-catalyzed enantioselective acylation with racemic N-alkyl-6-hydroxydodecanamide (rac-2) as a substrate was attempted. Lipase PS-catalyzed acetylation using rac-2 progressed efficiently, and both enantiomers of 1 were obtained with over 90% optical purities.