1. Supramolecular asymmetric induction : A new concept applied to the supported enantioselective synthesis of α-amino acids
- Author
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Habiba Ismaili, Monique Calmes, Jacques Daunis, Abdelhadi Zouanate, Robert Jacquier, Jean Koudou, and Gèrard Nkusi
- Subjects
inorganic chemicals ,Chiral auxiliary ,Schiff base ,Stereochemistry ,organic chemicals ,Organic Chemistry ,technology, industry, and agriculture ,Enantioselective synthesis ,Supramolecular chemistry ,Protonation ,Biochemistry ,Asymmetric induction ,chemistry.chemical_compound ,chemistry ,Drug Discovery ,polycyclic compounds ,heterocyclic compounds ,Enantiomer ,Chirality (chemistry) - 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.
- Published
- 1990
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