67198-86-1Relevant articles and documents
Ring opening of a trisubstituted aziridine with amines: Regio- and stereoselective formation of substituted 1,2-diamines
Kelley, Brandon T.,Joullie, Madeleine M.
supporting information; experimental part, p. 4244 - 4247 (2010/11/16)
Figure Presented. The formation of substituted 1,2-diamines via nucleophilic ring opening of a trisubstituted ethynyl aziridine was performed with complete regio- and stereoselective control. Various amines with different levels of nucleophilicity were employed and gave similar results. The ring opening reaction is not limited to ethynyl aziridines, as other alkyl trisubstituted aziridines gave the same results. This method allows for the formation of unique vicinal diamines while providing a fully substituted carbon center in a stereoselective manner under mild conditions.
A new stereocontrolled approach to a key intermediate in the synthesis of (25,3R)-capreomycidine
Martinkova, Miroslava,Gonda, Jozef,Dzoganova, Martina
, p. 1199 - 1210 (2008/03/27)
A new stereocontrolled approach to the synthesis of advanced intermediate in the synthesis of nonproteinogenic amino acid (2S,3R)-capreomycidine via the novel domino reaction has been developed.
Silylcupration of (R)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4- ethynyloxazolidine: A stereoselective approach to the synthesis of γ- silylated saturated and unsaturated α-amino acids
Reginato, Gianna,Mordini, Alessandro,Valacchi, Michela,Grandini, Elena
, p. 9211 - 9216 (2007/10/03)
Enantioselective synthesis of γ-silylated amino acids is reported, using a four-step procedure based on the silylcupration of ethynyloxazolidine 2. Silylcuprates 6a-c are highlighted as useful reagents to be employed with enantiomerically enriched substrates. Vinylsilanes 5 are easily prepared and highlighted as useful intermediates to yield the final compounds after reduction, opening of the oxazolidine ring, and oxidation. Moreover, β,γ- unsaturated amino acids are obtained as very interesting vinylglycine derivatives. The capability of silicon-containing amino acids to be incorporated into dipeptides is also shown.