A stereoselective entry into functionalized 1,2-diamines by zinc-mediated homologation of alpha-aminoacids.
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.
Hoang
Cam Thuy
CT
Laboratoire de Chimie des Procédés et Substances Naturelles, Institut de Chimie Moléculaire et des Matériaux d'Orsay (UMR CNRS 8182), Bâtiment 410, Université de Paris-Sud 11, F-91405 Orsay, France.
Alezra
Valérie
V
Guillot
Régis
R
Kouklovsky
Cyrille
C
D000596:Amino Acids / Q000737:chemistry*; D003959:Diamines / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D015032:Zinc / Q000737:chemistry*
D000596:Amino Acids; D003959:Diamines; D015032:Zinc