Amino Acids

, Volume 7, Issue 1, pp 105–108 | Cite as

Sulfenylation of chiral Schiff bases

  • A. Bentama
  • S. Hoarau
  • L. Pappalardo
  • M. L. Roumestant
  • P. Viallefont
Article

Summary

The purpose of this study was to examine the conditions of sulfenylation reactions of chiralα-amino esters Schiff bases to protect the chirality in theα-position.

Keywords

Amino acids Schiff bases 2-Hydroxypinan-3-one Sulfenylation Desulfenylation 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. El Achqar A, Roumestant ML, Viallefont P (1988) Reactions of Schiff base anions with electrophiles: role of the initial stereochemistry. Tetrahedron Lett 29: 2441–2444Google Scholar
  2. El Marini A, Roumestant ML, Pappalardo L, Viallefont P (1989) Utilisation des organocuprates dans la synthèse desα-aminoacides hétérocycliques. Bull Soc Chim Fr 4: 554–558Google Scholar
  3. Horner L, Doms G (1978) Studien zum Vorgang der Wasserstoffübertragung 51 Raneynickel als Reagenz zur hydrierenden Abspaltung des Chalkogenatoms aus Schwefel-Selen-und Tellur-Verbindungen. Phosphorus Sulfur 4: 259–265Google Scholar
  4. Newman MS, Walborsky HM (1950) Reduction ofα- andβ-ketoesters. JA Chem Soc 72: 4295–4297Google Scholar
  5. Oguri T, Kawai N, Shioiri T, Yamada S (1978) Aminoacids and peptides. XXIX. A new efficient derivatives with recycling of a chiral reagent, asymmetric alkylation of achiral Schiff base from glycine. Chem Pharm Bull 26: 803–808Google Scholar
  6. Schmidt H (1960) Spatial isomerism in the pinane series.VI. Hydroxypinocamphone and the two diastereoisomericα-pinene glycols. Chem Ber 93: 2485–2490Google Scholar
  7. Tabcheh M, El Achqar A, Pappalardo L, Roumestant ML, Viallefont P (1991) Alkylation and protonation of chiral Schiff bases: diastereoselectivity as a function of the nature of reactants. Tetrahedron 47: 4611–4618Google Scholar

Copyright information

© Springer-Verlag 1994

Authors and Affiliations

  • A. Bentama
    • 1
  • S. Hoarau
    • 1
  • L. Pappalardo
    • 1
  • M. L. Roumestant
    • 1
  • P. Viallefont
    • 1
  1. 1.Laboratoire Aminoacides et PeptidesURA 468, CNRS-Université Montpellier IIFrance

Personalised recommendations