Ether-directed palladium(II)-catalysed aza-Claisen rearrangements: studies on the origin of the directing effect

被引：24

作者：

Jamieson, Andrew G. ^{[1
]}

Sutherland, Andrew ^{[1
]}

机构：

[1] Univ Glasgow, Dept Chem, WestCHEM, Glasgow G12 8QQ, Lanark, Scotland

来源：

TETRAHEDRON | 2007年 / 63卷 / 10期

基金：

英国工程与自然科学研究理事会;

关键词：

palladium catalysis; aza-Claisen rearrangement; directing effect;

D O I：

10.1016/j.tet.2006.12.067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four new chiral delta-substituted allylic trichloroacetimidates have been synthesised to probe the origin of the high diastereoselectivity observed for the MOM-ether directed palladium(II)-catalysed aza-Claisen rearrangement. Rearrangement of these compounds has not only provided strong evidence for this directing effect but also that during the rearrangement both oxygen atoms from the MOM-ether are involved in coordinating to and directing the palladium(II) catalyst. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2123 / 2131

页数：9

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