137588-59-1Relevant articles and documents
A recyclable chiral auxiliary for the asymmetric syntheses of α-aminonitriles and α-aminophosphinic derivatives
Rossi, Jean-Christophe,Marull, Marc,Larcher, Nicolas,Taillades, Jacques,Pascal, Robert,van der Lee, Arie,Gerbier, Phillipe
, p. 876 - 883 (2008/09/21)
Optically active α-aminonitriles and α-aminophosphinic derivatives have been prepared in high yield and high ee using an easy route by extending our previously developed method involving the following sequence: (i) stereoselective Strecker condensation of
Influence of a Hydroalcoholic Solvent on the Enantioselectivity of α-Amino nitrile Hydration Catalysed by Chiral Ketones
Lagriffoul, Pierre-Henri,Tadros, Ziad,Taillades, Jacques,Commeyras, Auguste
, p. 1279 - 1285 (2007/10/02)
The enantioselective hydration of α-aminonitriles 1, RCH(CN)NH2 i; 1c: R = Ph> has been achieved in an alkaline hydroalcoholic medium in the presence of chiral ketonic catalysts.Of the different ketones used, (-)-(5R,3R,2R)-5-(methylethenyl)-3-cyano-2-methylcyclohexanone (8) gives rise to significant enantioselectivity D/kL = 2.1; T = 10 deg C; solvent, water-propan-2-ol (45:55,v/v)>.Although the structure of the catalyst could probably be improved, we show in this paper that the efficiency and especiallythe enantioselectivity of the catalyst are not only under steric control but also depend on the nature and composition of the hydroalcoholic solvent.Thus, for the three aminonitriles studied in the presence of the catalyst 8, the increase in percentage of propan-2-ol favours the hydration of the D α-aminonitrile as shown for the hydration of 1c for which the ratio kD/kL increases threefold when the percentage of propan-2-ol increases from 10 to 95percent.