期刊
TETRAHEDRON LETTERS
卷 43, 期 48, 页码 8647-8651出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(02)02135-4
关键词
oxybutynin; muscarinic receptor antagonist; alpha-hydroxy carboxylic acid; catalytic enantioselective cyanosilylation; ketones; practical synthesis
(S)-Oxybutynin, an important drug acting as muscarinic receptor antagonist, was practically synthesized using catalytic enantioselective cyanosilylation of cyclohexyl phenyl ketone (6a) as a key step. Cyanohydrin 7a with 94% ee was obtained with 1 mol% of Gd-5 catalyst. The key alpha-hydroxy carboxylic acid 8 was synthesized from 7a in an enantiomerically pure form without column chromatography. Other cycloalkyl phenyl ketones, except cyclopentyl phenyl ketone (6e-H) gave products with high enantio selectivity. The enantioselectivity of the reaction of 6e was dramatically improved using alpha-deuterium substituted 6e-D. The dramatic deuterium effect provides an important insight into the competitive reaction pathway. (C) 2002 Elsevier Science Ltd. All rights reserved.
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