N-Acyliminium ion chemistry and palladium catalysis: a useful combination to obtain bicyclic heterocycles

WFJ Karstens, D Klomp, FPJT Rutjes, H Hiemstra

Index: Karstens, Willem F.J.; Klomp, Dirk; Rutjes, Floris P.J.T.; Hiemstra, Henk Tetrahedron, 2001 , vol. 57, # 24 p. 5123 - 5130

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Citation Number: 41

Abstract

By using N-acyliminium ion chemistry, several ω-propadienyllactams and a propadienyloxazolidine were prepared from N-acyliminium ion precursors and propargylsilanes. Treatment of these allene containing lactams and oxazolidinone with allyl halides or an allyl carbonate using Pd (II)-salts as the catalyst gave rise to a coupling– cyclization reaction, yielding bicyclic systems in which the allyl moiety is incorporated. ...