Unusual Skeletal Rearrangement of Unsaturated Seven??Membered Lactams into Fused Pyrrolidinolactones

…, A Gradillas, J Pérez??Castells

Index: Alvarez, Silvia; Dominguez, Gema; Gradillas, Ana; Perez-Castells, Javier European Journal of Organic Chemistry, 2013 , # 15 p. 3094 - 3102

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Abstract

Abstract Unsaturated ϵ-lactams undergo a novel process involving a skeletal reorganization to give fused pyrrolidine-lactones by reaction with aromatic α-bromo ketones in the presence of 1, 4-diazabicyclo [2.2. 2] octane and a base. The process involves the formation of an ammonium salt and subsequently a nitrogen ylide, which initiates the rearrangement reaction. This species reduces undesired side-reactions such as double-bond shifts or ...