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

Aldimines of α-amino esters derived from aldehydes bearing an α-, β- or γ-protected amino group undergo AgOAc/R 3N catalysed cycloaddition to electronegative olefins (dipolarophile). Subsequent unmasking of the amino group and lactamisation, spontaneous in most cases, generates 5–7 membered fused an...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 58; no. 9; pp. 1719 - 1737
Main Authors Blaney, Paul, Grigg, Ronald, Rankovic, Zoran, Thornton-Pett, Mark, Xu, Juan
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 25.02.2002
Elsevier
Subjects
azomethine ylide
bridged and fused rings
Chemistry
Chemistry, Organic
cycloaddition
heterocycles
lactamisation
Physical Sciences
Science & Technology
bridged and fused rings
azomethine ylide
cycloaddition
lactamisation
heterocycles
POTENT
AMINO-ACIDS
RECEPTOR
Online AccessGet full text

Cover

More Information
Summary:Aldimines of α-amino esters derived from aldehydes bearing an α-, β- or γ-protected amino group undergo AgOAc/R 3N 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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00029-7