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


Medicinal Chemistry

Author(s): Kobayashi S, Kamiyama K, Ohno M

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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.
This article was published in Chem Pharm Bull (Tokyo) and referenced in Medicinal Chemistry

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