1,2-ASYMMETRIC INDUCTION IN THE KETENE CLAISEN REARRANGEMENT OF ALLYL SULFIDES

被引：31

作者：

NUBBEMEYER, U ^{[1
]}

OHRLEIN, R ^{[1
]}

GONDA, J ^{[1
]}

ERNST, B ^{[1
]}

BELLUS, D ^{[1
]}

机构：

[1] CIBA GEIGY AG,SCHWARZWALDALLEE 211,CH-4002 BASEL,SWITZERLAND

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1991年 / 30卷 / 11期

关键词：

D O I：

10.1002/anie.199114651

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Optically active alpha-siloxycarbonates are converted to optically active allylsulfides 1. These intermediates are allowed to react with dichloroketene (generated in situ) leading to optically active alpha,alpha-dichloro-beta-vinyl-gamma-siloxy-substituted thioesters 2. The assumed transition state is represented by 3. This ketene-Claissen rearrangement shows complete 1,2-asymmetric induction in all of the cases examined. Reductive dechlorination of the gamma-siloxy-substituted thioesters provides optically active 3,4-cis-distubstituted gamma-lactones. R = Me, iPr, C2H4OTBDMS: TBDMS = teri-butyldimethylsilyl.

引用

页码：1465 / 1467

页数：3

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