Highly diastereoselective conjugate addition to alkylidene Bis(Sulfoxides):: Asymmetric synthesis of (+)-erythro-roccellic acid

被引：41

作者：

Brebion, F

Delouvrié, B

Nájera, F

Fensterbank, L

Malacria, M

Vaissermann, J

机构：

[1] Univ Paris 06, CNRS, Chim Organ Lab, UMR 7611, F-75252 Paris 05, France

[2] Univ Paris 06, CNRS, Lab Chim Inorgan & Mat Mol, UMR 7071, F-75252 Paris 05, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 43期

关键词：

allylic compounds; asymmetric synthesis; Michael addition; sulfoxides; total synthesis;

D O I：

10.1002/anie.200352356

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Facial stereocontrol is possible in Michael additions of nucleophiles (Nu) to alkylidene bis(sulfoxides), which proceed via nonchelated (A) or chelated (B) intermediates depending on the addition of an appropriate Lewis acid (LA). This intriguing reactivity could be applied to the first total synthesis of the succinate-based natural product, (+)-erythro-roccellic acid.

引用

收藏

页码：5342 / 5345

页数：4

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