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.
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页码：1719 / 1737
页数：19
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