The Benzyne Aza-Claisen Reaction

被引：105

作者：

Cant, Alastair A. ^{[1
]}

Bertrand, Guillaume H. V. ^{[1
]}

Henderson, Jaclyn L. ^{[1
]}

Roberts, Lee ^{[2
]}

Greaney, Michael F. ^{[1
]}

机构：

[1] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland

[2] Pfizer Global R&D, Discovery Chem, Sandwich, Kent, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 28期

基金：

英国工程与自然科学研究理事会;

关键词：

allylamines; arynes; aza-Claisen rearrangement; medium-ring compounds; CYCLIC ALPHA-VINYLAMINES; 9-MEMBERED RING LACTAMS; SIGMA-BONDS; DIMETHYL ACETYLENEDICARBOXYLATE; 3-AZA-COPE REARRANGEMENT; TRANSANNULAR REACTIONS; MILD CONDITIONS; ARYNES; DERIVATIVES; CYCLIZATION;

D O I：

10.1002/anie.200901410

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Adding an aryne to a tertiary allylamine affords oallylaniline products of an aza-Claisen rearrangement. The aryne simultaneously provides the π component for the rearrangement and the quaternization event that lowers the activation energy for the sigmatropic shift. The reaction was applied to the synthesis of medium-ring benzannulated amines (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5199 / 5202

页数：4

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