Volume 24, Issue 4
Heterocyclic Compounds
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ChemInform Abstract: Asymmetric Twin-Ring Differentiation by Lipase-Catalyzed Enantiotoposelective Reaction of the Ring-Crossed meso Glycol: Asymmetric Synthesis of a Highly Functionalized Piperidine from the Conjoined Twin Piperidine System.

T. MOMOSE

T. MOMOSE

Fac. Pharm. Sci., Toyama Med. Pharm. Univ., Toyama 930-01, Japan

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N. TOYOOKA

N. TOYOOKA

Fac. Pharm. Sci., Toyama Med. Pharm. Univ., Toyama 930-01, Japan

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M. JIN

M. JIN

Fac. Pharm. Sci., Toyama Med. Pharm. Univ., Toyama 930-01, Japan

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First published: January 26, 1993

Abstract

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ChemInform Abstract

Lipase-catalyzed transesterification reaction of the diol (I) with vinyl acetate (II) affords the almost optically pure chiral monoacetate (III) which is further oxidized to give the ketone (IV). This ketone (IV) is cleaved to form the derivative (VI) of the desired chiral piperidine mentioned in the title. The enantiomer of (VI) is obtained via lipase catalyzed selective hydrolysis of the diacetate.

chemical structure image

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