1. Synthesis of cis-5-Trifluoromethylproline from l-Glutamic Acid
- Author
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Rajesh Dave, Stéphanie Ortial, David Bénimélis, Patrick Meffre, Zohra Benfodda, Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Calyx Chemicals and pharmaceuticals Ltd, Calyx Chemicals and pharmaceutics, Laboratoire de Chimie BioOrganique / Université de Nîmes (LCBO), Université de Nîmes (UNIMES), HPLC separations (ISM2-UMR 7313, and Aix-Marseille Université.
- Subjects
chemistry.chemical_classification ,amino acids ,5-trifluoromethylproline ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,010405 organic chemistry ,Stereochemistry ,Trifluoromethylation ,Organic Chemistry ,Imine ,Linear sequence ,chemistry.chemical_element ,cis-5-trifluoromethylproline ,reduction ,Glutamic acid ,010402 general chemistry ,01 natural sciences ,Aldehyde ,0104 chemical sciences ,Amino acid ,chemistry.chemical_compound ,chemistry ,fluorine ,Fluorine ,diastereoselective synthesis ,imine - Abstract
International audience; 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.
- Published
- 2014
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