Arkivoc

Use of the cascade α-oxo-amidoalkylation/transposition/π-cationic cyclization of N-acyliminium ions in the synthesis of novel fused heterocyclic N, O-acetals

A Pesquet, L Van Hijfte, A Daïch

Index: Pesquet, Anthony; Van Hijfte, Luc; Daich, Adam Arkivoc, 2010 , vol. 2010, # 8 p. 27 - 40

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Citation Number: 3

Abstract

Abstract Tricyclic N, O-acetal scaffolds have been prepared easily in few steps starting from cheap reagents in moderate to good yields (40-68%) in which the α-hydroxy lactam intermediates constitute the key substrates. These cyclized products are the result of the exclusive intramolecular attack of the oxygen atom onto the endocyclic N-acyliminium ion intermediates leading to the new cyclic aza-oxonium salts, their opening into exocyclic N- ...