75984-69-9Relevant academic research and scientific papers
Derecemization par protonation enantioselective. Application a un α-aminoacide, la phenylglycine
Duhamel, Lucette,Plaquevent, Jean-Christophe
, p. 75 - 83 (2007/10/02)
This work describes the application of deracemization by enantioselective protonation to α-aminoacid derivatives.Esters of phenylglycine are readly converted into Schiff bases.Melanation of the latter by a lithium amide, followed by protonation by a chiral acid, leads to the optically active starting materials (e.e. as high as 70percent).Chiral acids can easily be retrieved after protonation with excellent yields and conservation of enantiomeric purity.A mechanism responsible for the asymmetric induction is suggested by means of a study of the parameters modifying the selectivity, such as the nature of protecting groups, chiral acid, and lithium amide.
