Cascade cyclization intermolecular dipolar cycloaddition by multi-component couplings—synthesis of indolizidines and pyrrolizidines

I Coldham, S Jana, L Watson, CD Pilgram

Index: Coldham, Iain; Jana, Samaresh; Watson, Luke; Pilgram, Christopher D. Tetrahedron Letters, 2008 , vol. 49, # 37 p. 5408 - 5410

Full Text: HTML

Citation Number: 27

Abstract

A three-component coupling reaction of a primary amine (an amino-acid or amino-ester or hydroxylamine), an alkene or alkyne dipolarophile and an aldehyde bearing a halide as a leaving group has been developed. Condensation of the amine with the aldehyde and cyclization (intramolecular N-alkylation) provides, after decarboxylation or deprotonation, a cyclic azomethine ylide (or nitrone) that undergoes intermolecular dipolar cycloaddition ...