title: Access to optically active 3-azido- and 3-aminopiperidine derivatives by enantioselective ring expansion of prolinols.
abstract: The activation of N-alkyl prolinols by XtalFluor E allowed the formation of an aziridinium intermediate that can react with tetrabutylammonium azide (nBu(4)NN(3)) to produce 3-azidopiperidines and/or 2-(azidomethyl)pyrrolidines, in a ratio up to 100/0. These 3-azidopiperidines can be reduced to the corresponding 3-aminopiperidines.
authors.affiliation: Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS (UMR 7084) 10 rue Vauquelin, 75231-Paris Cedex 05, France.
authors.forename: Anne
authors.initials: A
authors.lastname: Cochi
authors.forename: Domingo Gomez
authors.initials: DG
authors.lastname: Pardo
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
mesh_terms: D000588:Amines / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds; D010084:Oxidation-Reduction; D010880:Piperidines / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D001386:Azides; D009942:Organometallic Compounds; D010880:Piperidines; D011759:Pyrrolidines; C508266:azido ruthenium; C010509:prolinol; C032727:piperidine