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Communication | Special issue | Vol 52, No. 3, 2000, pp.1029-1032
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S122
Kinetic Resolution of cis-3-Alkylcyclohexene Oxide by a Chiral Lithium Amide - An Application to a Synthesis of Both Enantiomers of Isomenthon -

Masatoshi Asami,* Shinsuke Sato, Kiyoshi Honda, and Seiichi Inoue

*Department of Chemistry and Biotechnology, Faculty of Engineering, Yokohama National University, Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan

Abstract

Kinetic resolution of cis-3-alkylcyclohexene oxide (1) was examined using chiral lithium amide, lithium (S)-2-(pyrrolidin-1-yl)methylpyrrolidide (2). High ee (84Æ98% ee) of 1 was obtained by using 1.1-1.2 equiv of 2, while 6-alkyl-2-cyclohexenol (3) was obtained in moderate ee (60-68% ee) by using 0.5-0.75 equiv of 2. Both enantiomers of cis-2-isopropyl-5-methylcyclohexanone (isomenthone) were derived from (1S,2R,3R)-(+)-3-isopropylcyclohexene oxide (1b) or (1R,6R)-(-)-6-isopropyl-2-cyclohexenol (3b) in a few steps, respectively.