Efficient synthesis of polyfunctionalised enantiopure diazepanone scaffolds

O Monasson, M Ginisty, G Bertho, C Gravier-Pelletier…

Index: Monasson, Olivier; Ginisty, Maryon; Bertho, Gildas; Gravier-Pelletier, Christine; Le Merrer, Yves Tetrahedron Letters, 2007 ,  vol. 48,  # 46  p. 8149 - 8152

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Citation Number: 21

Abstract

The synthesis of polyfunctionalised enantiopure 1, 4-diazepan-3-one scaffolds from l-serine derivatives and azidoepoxides readily available from either l-ascorbic or d-isoascorbic acid, allowing access to various configurations at chiral centres, is described. The key steps are the nucleophilic opening of the epoxide by the amine of serine followed by a lactonisation– lactamisation sequence.