Tetrahedron letters

A stereoselective intramolecular retro-ene reaction catalysed by aluminium chloride

M Bodajla, GR Jones, CA Ramsden

Index: Bodajla, Michal; Jones, Graeme R.; Ramsden, Christopher A. Tetrahedron Letters, 1997 , vol. 38, # 14 p. 2573 - 2576

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Citation Number: 16

Abstract

Reaction of 5-(2-naphthalenol)-1-pentenes with I (III) reagents results in nucleophilic substitution at C-1 rather than [4+ 2] intramolecular ionic cycloaddition of the proposed intermediate arenoxenium cations. Treatment of the same precursors with aluminium chloride results in a stereoselective intramolecular cyclisation to spiroketones. Evidence that the mechanism of formation involves a cyclic aluminium intermediate is presented.© 1997 ...