Chemical & Pharmaceutical Bulletin 1990-02-01

Chiral synthon obtained with pig liver esterase: introduction of chiral centers into cyclohexene skeleton.

S Kobayashi, K Kamiyama, M Ohno

Index: Chem. Pharm. Bull. 38(2) , 350-4, (1990)

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Abstract

A versatile chiral synthon, (1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid, was obtained by an enantioselective hydrolysis of the corresponding meso diester with pig liver esterase. This enzymatic hydrolysis can easily be carried out on a multi-hundred gram scale. The chiral monoester thus obtained can be further converted into all stereoisomers of 1-amino-2-alkoxycarbonyl-4-cyclohexene derivatives in an enantio- and stereocontrolled manner. These derivatives are considered as potential key intermediates for synthesizing a variety of biologically interesting compounds such as aminocyclitol and carbapenem antibiotics.