A stereoselective entry into functionalized 1,2-diamines by zinc-mediated homologation of alpha-aminoacids |
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Authors: | Hoang Cam Thuy Alezra Valérie Guillot Régis Kouklovsky Cyrille |
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Institution: | Laboratoire de Chimie des Procédés et Substances Naturelles, Institut de Chimie Moléculaire et des Matériaux d'Orsay (UMR CNRS 8182), Batiment 410, Université de Paris-Sud 11, F-91405 Orsay, France. |
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Abstract: | A general, stereoselective synthesis of 4,5-disubstituted imidazolidines-2-ones from alpha-aminoacids has been developed: the key steps are a Blaise reaction of bromoacetate on alpha-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 stereoselectivity. Acidic hydrolysis of the urea gave 4-amino-pyrrolidinones, which can be precursors to beta,gamma-diaminoacids or 3-aminopyrrolidines. |
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