Applications of highly enantioenriched alcohols bearing a phenylthio group in the preparation of ring compounds. The two-pot synthesis of an enantiopure spiroacetal pheromone bearing three chiral centers

被引：22

作者：

Cohen, T

Tong, SJ

机构：

[1] Department of Chemistry, University of Pittsburgh, Pittsburgh

来源：

TETRAHEDRON | 1997年 / 53卷 / 28期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4020(97)00635-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The new chiron (S)-6-phenylthio-2-hexanol (3) was prepared in high enantiomeric excess by baker's yeast reduction of the corresponding ketone. Enantioenriched alcohols 1, 2 and 3, prepared previously by a similar procedure, or their racemic counterparts, were transformed into ring closed compounds 5-methyl-2-(phenylthio)tetrahydrofuran (9), 6-methyl-2-(phenylthio)tetrahydropyran (10), 2-methyl-1-phenylsulfonyl cyclopropane (14), cyclobutane (15), cyclopentane (16), and a bee pheromone, (2S,6R,8S)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane (20). (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：9487 / 9496

页数：10

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