Organic letters

A stereoselective entry into functionalized 1, 2-diamines by zinc-mediated homologation of α-aminoacids

CT Hoang, V Alezra, R Guillot, C Kouklovsky

Index: Hoang, Cam Thuy; Alezra, Valerie; Guillot, Regis; Kouklovsky, Cyrille Organic Letters, 2007 , vol. 9, # 13 p. 2521 - 2524

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Citation Number: 30

Abstract

A general, stereoselective synthesis of 4, 5-disubstituted imidazolidines-2-ones from α- aminoacids has been developed: the key steps are a Blaise reaction of bromoacetate on α- aminonitriles and further reduction. Although reduction with sodium cyanoborohydride afforded a mixture of cis and trans isomers 6a-e with moderate to good stereoselectivity, reduction with sodium in liquid ammonia gave the trans isomers 8a-e with complete ...