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Enzyme-mediated enantioselective hydrolysis of cyclic carbonates bearing an unsaturated substituent

✍ Scribed by Kazutsugu Matsumoto; Yasuhide Nakamura; Megumi Shimojo; Minoru Hatanaka

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 75 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01628-3

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✦ Synopsis

A new method for the preparation of optically active five-membered cyclic carbonates bearing an unsaturated substituent via an enzymatic reaction is described. In the examination of the regiospecific recognition of PPL, dl-(E)-4-(1-octenyl)-1,3-dioxolan-2-one is hydrolyzed with higher enantioselectivity. The reaction is also applicable to the racemic (E)-4-[2-(alkoxycarbony)ethenyl]-1,3-dioxolane-2-one, a useful a,b-unsaturated ester in organic syntheses. Introducing the isopropyl group to the ester moiety affords the highest enantioselectivity although the ester group is located at a remote position from the asymmetric carbon.

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