SEQUENTIAL DIASTEREOSELECTIVE ADDITION AND PALLADIUM(II)-CATALYZED ALLYLIC ACETATE TRANSPOSITION OF SYN AND ANTI-ALPHA-ACETOXY-BETA-SILYL-(E)-HEX-4-ENOATES WITH ACHIRAL ACETALS - ASYMMETRIC-SYNTHESIS OF DIFFERENTIATED SYN AND ANTI-1,3-DIOL SYNTHONS

被引：34

作者：

PANEK, JS

YANG, M

SOLOMON, JS

机构：

[1] Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, Boston

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 05期

关键词：

D O I：

10.1021/jo00057a008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

syn- and anti-methyl alpha-acetoxy-beta-(dimethylphenylsilyl)-(E)-hex-4-enoates, (2R,3R)-8a and (2S,3R)-8b, undergo highly diastereo- and enantioselective addition reactions with aldehydes and acetals 11 catalyzed by the action of trimethylsilyl trifluoromethanesulfonate (TMSOTf) generating alpha-acetoxy-beta,-gamma-unsaturated esters (allylic acetates) 12. A subsequent allylic acetate transposition promoted by dichloropalladium bisacetonitrile complex, PdCl2(MeCN)2 afforded the differentiated 1,3-diol synthons 13.

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页码：1003 / 1010

页数：8

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