Tetrahedron

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

P Blaney, R Grigg, Z Rankovic, M Thornton-Pett, J Xu

Index: Blaney, Paul; Grigg, Ronald; Rankovic, Zoran; Thornton-Pett, Mark; Xu, Juan Tetrahedron, 2002 , vol. 58, # 9 p. 1719 - 1737

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Citation Number: 32

Abstract

Aldimines of α-amino esters derived from aldehydes bearing an α-, β-or γ-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.