Full Paper

A Concise Stereoselective Synthesis of 2-Substituted 1-Aminocyclopropanecarboxylic Acids

  1. Tarun K. Pradhan1,
  2. Antoine Joosten1,
  3. Jean-Luc Vasse1,
  4. Philippe Bertus2,
  5. Philippe Karoyan3,
  6. Jan Szymoniak1

Article first published online: 27 AUG 2009

DOI: 10.1002/ejoc.200900656

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2009, Issue 29, pages 5072–5078, October 2009

Additional Information

How to Cite

Pradhan, T. K., Joosten, A., Vasse, J.-L., Bertus, P., Karoyan, P. and Szymoniak, J. (2009), A Concise Stereoselective Synthesis of 2-Substituted 1-Aminocyclopropanecarboxylic Acids. European Journal of Organic Chemistry, 2009: 5072–5078. doi: 10.1002/ejoc.200900656

Author Information

  1. 1

    ICMR, CNRS-UMR 6229, Université de Reims Champagne-Ardenne, BP 1039, 51687 Reims Cedex 2, France, Fax: +33-(0)3-26-91-31-66

  2. 2

    CNRS-UMR 6011, UCO2M, Université du Maine, 72085 Le Mans Cedex 9, France

  3. 3

    CNRS-UMR 7613, UPMC, Université Paris 06, 75 252 Paris Cedex 05, France

Publication History

  1. Issue published online: 28 SEP 2009
  2. Article first published online: 27 AUG 2009
  3. Manuscript Received: 16 JUN 2009

Funded by

  • Ministère de l'Education Nationale et de la Recherche
  • ANR (Agence Nationale de Recherche)

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article with Supporting Information (HTML) Get PDF (199K)

Keywords:

  • Amino acids;
  • Peptidomimetics;
  • Diastereoselectivity;
  • Small ring systems;
  • Titanium

Graphical Abstract

Thumbnail image of graphical abstract

A short and stereoselective synthetic pathway to synthesize cyclopropane aminoacids derived from proteinogenic α-amino acids or analogues has been developed.

Abstract

A simple and stereoselective method for the preparation of (Z)-2-substituted 1-aminocyclopropanecarboxylic acids is described. The common key step for these reaction sequences involves the stereoselective Ti-mediated coupling of benzyloxy nitrile and homoallylic alcohol. The resulting 2-hydroxyethyl-substituted cyclopropylamine can be transformed shortly into various cyclopropane amino acid analogues on the gram scale, in good overall yields. Several syntheses of 2,3-methanoamino acids, that is, ACCs derived from proteinogenic α-amino acids or analogues, such as glutamic acid, arginine, homoarginine, and lysine derivatives are presented to exemplify the usefulness of the method. Additionally, starting from cyanoesters, spirocyclopropane γ-amino acid analogues are available in this way. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

View Full Article with Supporting Information (HTML) Get PDF (199K)