Tetrahedron

Functionalisation of pyrrolidin-2-ones at C4 and C5

CJ Easton, MJ Pitt, CM Ward

Index: Easton, Christopher J.; Pitt, Michael J.; Ward, Caroline M. Tetrahedron, 1995 , vol. 51, # 46 p. 12781 - 12790

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Citation Number: 11

Abstract

Treatment of pyrrolidin-2-ones with N-bromosuccinimide affords the corresponding 4, 5- dibromo-γ-lactams. The introduced bromo substituents may be selectively displaced in ionic and radical reactions. The synthetic utility of this procedure is illustrated in regioselective elaborations of the dibromides, including the generation of a bicyclic tetrahydrofuropyrrolidinone system.