Fused and bridged bi- and tri-cyclic lactams via sequential metallo-azomethine ylide cycloaddition-lactamisation

被引：30

作者：

Blaney, P

Grigg, R ^{[1
]}

Rankovic, Z

Thornton-Pett, M

Xu, J

机构：

[1] Univ Leeds, Sch Chem, Mol Innovat Divers & Automated Synthesis Ctr, Leeds LS2 9JT, W Yorkshire, England

[2] Organon Labs, Newhouse ML1 5SH, Lanark, Scotland

来源：

TETRAHEDRON | 2002年 / 58卷 / 09期

基金：

英国工程与自然科学研究理事会;

关键词：

azomethine ylide; cycloaddition; heterocycles; lactamisation; bridged and fused rings;

D O I：

10.1016/S0040-4020(02)00029-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aldimines of a-amino esters derived from aldehydes bearing an alpha-, beta- or gamma-protected amino group undergo AgOAc/R3N catalysed cycloaddition to electronegative olefins (dipolarophile). Subsequent unmasking of the amino group and lactamisation, spontaneous in most cases, generates 5-7 membered fused and bridged bi- and tri-cyclic lactams. The regioselectivity of the lactamisation is controlled by appropriate choice of the dipolarophile. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1719 / 1737

页数：19