HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF SUBSTITUTED EPICHLOROHYDRINS AND REGIOSELECTIVE PREPARATION OF ALLYL ALCOHOLS USING CHLORO OR IODOMETHYLLITHIUM

被引：14

作者：

CONCELLON, JM

LLAVONA, L

BERNAD, PL

机构：

[1] Instituto de Química Organometálica Enrique Moles, Facultad de Química, Universidad de Oviedo

来源：

TETRAHEDRON | 1995年 / 51卷 / 19期

关键词：

D O I：

10.1016/0040-4020(95)90943-Q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substituted epichlorohydrins 3 or 6 are obtained from alpha-bromo or alpha-chlorocarbonyl compounds (1 or 4) and chloro or iodomethyllithium, respectively. Starting from alpha-bromocarbonyl compounds 1 or acyclic alpha-chloro ketones the reaction takes place with total diastereoselectivity. Treatment of epichlorohydrins 3 or 6 with lithium iodide affords the same substituted allyl alcohols 7 in a regioselective manner. A mechanism to explain this transformation is proposed. Regioisomeric allyl alcohols 11 are prepared by reaction of epichlorohydrins 6 with lithium powder.

引用

页码：5573 / 5584

页数：12

共 50 条

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ALTENBACH HJ, 1991, FUNCTIONAL GROUP TRA, V6, P829

[2] A STEREOSPECIFIC ROUTE TO FUNCTIONALIZED ALKENES FROM TETRAHYDROFURFURYLIC ACETATES - SYNTHESIS OF PHEROMONES [J].