Carbamoyl Radical??Mediated Synthesis and Semipinacol Rearrangement of β??Lactam Diols

…, L Male, JW Steed, RS Grainger

Index: Betou, Marie; Male, Louise; Steed, Jonathan W.; Grainger, Richard S. Chemistry - A European Journal, 2014 , vol. 20, # 21 p. 6505 - 6517

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Citation Number: 10

Abstract

Abstract In an approach to the biologically important 6-azabicyclo [3.2. 1] octane ring system, the scope of the tandem 4-exo-trig carbamoyl radical cyclization—dithiocarbamate group transfer reaction to ring-fused β-lactams is evaluated. β-Lactams fused to five-, six-, and seven-membered rings are prepared in good to excellent yield, and with moderate to complete control at the newly formed dithiocarbamate stereocentre. No cyclization is ...