Tetrahedron p. 6021 - 6032 (1990)
Update date:2022-07-30
Topics:
Calmes, Monique
Daunis, Jacques
Ismaili, Habiba
Jacquier, Robert
Koudou, Jean
et al.
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.
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