Sequential olefin metathesis - Intramolecular asymmetric Heck reactions in the synthesis of polycycles

被引：12

作者：

Lautens, M ^{[1
]}

Zunic, V ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5H 3H6, Canada

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2004年 / 82卷 / 02期

关键词：

asymmetric; Heck; polycycles; metathesis; stereoselective; desymmetrization;

D O I：

10.1139/V03-196

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Application of the intramolecular asymmetric Heck reaction in the desymmetrization of a novel class of symmetrical bicyclodienes, synthesized through a diastereoselective double ring-closing metathesis (DSRCM) reaction, was achieved with good yields (approximately 80%) and excellent enantioselectivities (up to 99% ee). Three contiguous stereocenters are established in a single desymmetrization reaction. The use of thallium carbonate as base in the asymmetric Heck reaction favours double bond migration in 13. Cationic conditions delivered products with good to excellent enantioselectivities, surpassing the results under neutral conditions.

引用

页码：399 / 407

页数：9

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