Organic letters

Au-Catalyzed Synthesis of 5, 6-Dihydro-8 H-indolizin-7-ones from N-(Pent-2-en-4-ynyl)-β-lactams

Y Peng, M Yu, L Zhang

Index: Peng, Yu; Yu, Meng; Zhang, Liming Organic Letters, 2008 , vol. 10, # 22 p. 5187 - 5190

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Citation Number: 29

Abstract

Au-catalyzed synthesis of 5, 6-dihydro-8 H-indolizin-7-ones from readily available N-(pent-2- en-4-ynyl)-β-lactams is developed. In this reaction, a 5-exo-dig cyclization of the β-lactam nitrogen to the Au-activated C− C triple bond is followed by heterolytic fragmentation of the amide bond, forming a highly nucleophilic acyl cation. An expedient formal synthesis of indolizidine 167B was easily achieved using this new method.