944914-05-0Relevant articles and documents
AmIno Acid Homologation by the Blaise Reaction: A new entry into nitrogen heterocycles
Cam, Thuy Hoang,Bouillere, Francelin,Johannesen, Sine,Zulauf, Anais,Panel, Cecilia,Pouilhes, Annie,Gori, Didier,Alezra, Valerie,Kouklovsky, Cyrille
body text, p. 4177 - 4187 (2009/09/08)
(Chemical Equation Presented) A general strategy for the amino acid homologation via Blaise reaction and subsequent reduction is presented. This strategy involves the preparation of protected α-amino nitriles from the corresponding amino acids, followed by the zinc-mediated condensation of tert-butyl bromoacetate, to give the imidazolidones after iminozincate cyclization. Reduction gave the saturated imidazolidinones with cis or trans stereochemistry, depending on the reduction conditions. This strategy was applied to nonfunctionalized amino acids and to functionalized amino acids such as serine and aspartic acid. Additionally, acidic hydrolysis of cis or trans imidazolidinones to the corresponding chiral 4-aminopyrrolidones is described.
A Stereoselective entry into functionalized 1,2-diamines by zinc-mediated homologation of α-aminoacids
Hoang, Cam Thuy,Alezra, Valerie,Guillot, Regis,Kouklovsky, Cyrille
, p. 2521 - 2524 (2008/02/05)
A general, stereoselective synthsis of 4,5-disubstituted imidazolidines-2-ones from α-aminoacids has been developed: the key steps are a Biaise 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 stereoselectivity. Acidic hydrolysis of the urea gave 4-amino-pyrrolidinones, which can be precursors to β,γ-diaminoacids or 3-aminopyrrolidines.
