title: Stereoselective Rearrangement of (Trifluoromethyl)prolinols to Enantioenriched 3-Substituted 2-(Trifluoromethyl)piperidines.
abstract: 3-Substituted 2-(trifluoromethyl)piperidines B were synthesized by ring expansion of (trifluoromethyl)prolinols A, which were obtained from L-proline via an aziridinium intermediate C. The ring opening of the (trifluoromethyl)aziridinium intermediate by different nucleophiles is regio- and diastereoselective.
authors.affiliation: †Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), UMR 8231 ESPCI ParisTech/CNRS/PSL Research University, 10 rue Vauquelin, 75231-Paris Cedex 05, France.
authors.forename: Sarah
authors.initials: S
authors.lastname: Rioton
authors.affiliation: †Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), UMR 8231 ESPCI ParisTech/CNRS/PSL Research University, 10 rue Vauquelin, 75231-Paris Cedex 05, France.
authors.forename: Aurélie
authors.initials: A
authors.lastname: Orliac
authors.affiliation: ‡Laboratoire GlaxoSmithKline 100 Route de Versailles, 78160 Marly le-Roi, France.
authors.forename: Zeina
authors.initials: Z
authors.lastname: Antoun
authors.affiliation: ‡Laboratoire GlaxoSmithKline 100 Route de Versailles, 78160 Marly le-Roi, France.
authors.forename: Roselyne
authors.initials: R
authors.lastname: Bidault
authors.affiliation: †Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), UMR 8231 ESPCI ParisTech/CNRS/PSL Research University, 10 rue Vauquelin, 75231-Paris Cedex 05, France.
authors.forename: Domingo
authors.initials: D
authors.lastname: Gomez Pardo
authors.affiliation: †Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), UMR 8231 ESPCI ParisTech/CNRS/PSL Research University, 10 rue Vauquelin, 75231-Paris Cedex 05, France.
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D010880:Piperidines; D011759:Pyrrolidines; D011392:Proline