6037-42-9Relevant articles and documents
SUPRAMOLECULAR ASYMMETRIC INDUCTION : A NEW CONCEPT APPLIED TO THE SUPPORTED ENANTIOSELECTIVE SYNTHESIS OF α-AMINO ACIDS
Calmes, Monique,Daunis, Jacques,Ismaili, Habiba,Jacquier, Robert,Koudou, Jean,et al.
, p. 6021 - 6032 (1990)
A polyacrylic resin with pendant chirality has been used as a chiral auxiliary.The prochiral ester enolate, reversibly linked to the polymer chain via a Schiff base, is surrounded by chiral pendants, allowing supramolecular asymmetric induction to occur.Amino acids with enantiomeric excesses up to 88-89percent could be synthesized from supported glycine t-butyl ester enolate by reaction with alkyl halides.Enantioselective protonation depends on the initial configuration of the supported amino acid.Alanine was obtained in 90percent ee by repetitive asymmetric protonation.