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Synlett 2014; 25(4): 569-573
DOI: 10.1055/s-0033-1340553
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of cis-5-Trifluoromethylproline from l-Glutamic Acid

Stéphanie Ortial
a   Institut des Biomolécules Max Mousseron (IBMM), UMR CNRS 5247, Université de Montpellier I & II, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France
b   UNIVERSITE DE NIMES, Laboratoire de Chimie BioOrganique (LCBO), Place G. Péri, 30021 Nîmes Cedex 1, France   Fax: +33(4)66364587   eMail: patrick.meffre@unimes.fr
,
Rajesh Dave
,
Zohra Benfodda
a   Institut des Biomolécules Max Mousseron (IBMM), UMR CNRS 5247, Université de Montpellier I & II, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France
b   UNIVERSITE DE NIMES, Laboratoire de Chimie BioOrganique (LCBO), Place G. Péri, 30021 Nîmes Cedex 1, France   Fax: +33(4)66364587   eMail: patrick.meffre@unimes.fr
,
David Bénimélis
a   Institut des Biomolécules Max Mousseron (IBMM), UMR CNRS 5247, Université de Montpellier I & II, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France
b   UNIVERSITE DE NIMES, Laboratoire de Chimie BioOrganique (LCBO), Place G. Péri, 30021 Nîmes Cedex 1, France   Fax: +33(4)66364587   eMail: patrick.meffre@unimes.fr
,
Patrick Meffre*
a   Institut des Biomolécules Max Mousseron (IBMM), UMR CNRS 5247, Université de Montpellier I & II, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France
b   UNIVERSITE DE NIMES, Laboratoire de Chimie BioOrganique (LCBO), Place G. Péri, 30021 Nîmes Cedex 1, France   Fax: +33(4)66364587   eMail: patrick.meffre@unimes.fr
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Publikationsverlauf

Received: 03. November 2013

Accepted after revision: 09. Dezember 2013

Publikationsdatum:
14. Januar 2014 (online)

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Abstract

The diastereoselective synthesis of cis-5-trifluoromethylproline (5-Tfm-Pro) from l-glutamic acid is described. 5-Tfm-Pro could be obtained through a seven-step linear sequence. Trifluoromethylation of the glutamic-derived ester or aldehyde and subsequent reduction of the cyclic imine are the key steps in the synthesis.

Key words

amino acids - cis-5-trifluoromethylproline - fluorine - ­diastereoselective synthesis - imine - reduction

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett. Included are detailed experimental procedures and 1H NMR, 13C NMR, 19F NMR and HRMS data.
  • Supporting Information
 

  • References and Notes

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