Stereoselective Rearrangement of (Trifluoromethyl)prolinols to Enantioenriched 3-Substituted 2-(Trifluoromethyl)piperidines

Sarah Rioton; Aurélie Orliac; Zeina Antoun; Roselyne Bidault; Domingo Gomez Pardo; Janine Cossy

doi:10.1021/acs.orglett.5b01084

Stereoselective Rearrangement of (Trifluoromethyl)prolinols to Enantioenriched 3-Substituted 2-(Trifluoromethyl)piperidines

Org Lett. 2015 Jun 19;17(12):2916-9. doi: 10.1021/acs.orglett.5b01084. Epub 2015 May 22.

Authors

Sarah Rioton¹, Aurélie Orliac¹, Zeina Antoun², Roselyne Bidault², Domingo Gomez Pardo¹, Janine Cossy¹

Affiliations

¹ †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.
² ‡Laboratoire GlaxoSmithKline 100 Route de Versailles, 78160 Marly le-Roi, France.

PMID: 26000643
DOI: 10.1021/acs.orglett.5b01084

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aziridines / chemistry*
Molecular Structure
Piperidines / chemical synthesis*
Piperidines / chemistry
Proline / chemistry*
Pyrrolidines / chemistry*
Stereoisomerism

Substances

Aziridines
Piperidines
Pyrrolidines
Proline