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Reference type: Journal
Authors: Calmes M, Ismaili H, Jacquier R, Koudou J, Nkusi G, Zouanate A
Article Title: Supramolecular asymmetric induction : A new concept applied to the supported enantioselective synthesis of a-amino acids.
Publication date: 1990
Journal: Tetrahedron
Volume: 46
Issue: (17)
Page numbers: 6021-6032.
DOI: 10.1016/S0040-4020(01)87926-6

Abstract: 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 88-89% 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 aminoacid. Alanine was obtained in 90% ee by repetitive asymmetric protonation

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