title: Enantioselective synthesis of β-fluoroamines from β-amino alcohols: application to the synthesis of LY503430.
abstract: N,N-Dialkyl-β-amino alcohols were enantiospecifically and regioselectively rearranged by using N,N-diethylaminosulfur trifluoride (DAST) to give optically active β-fluoroamines in excellent yields and enantiomeric excesses. This rearrangement was applied to the enantioselective synthesis of LY503430, a potential therapeutic agent for Parkinson's disease.
authors.affiliation: Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Béranger
authors.initials: B
authors.lastname: Duthion
authors.forename: Domingo
authors.initials: D
authors.lastname: Gomez Pardo
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
mesh_terms: D000577:Amides / Q000138:chemical synthesis*; D000588:Amines / Q000138:chemical synthesis*; D000605:Amino Alcohols / Q000737:chemistry*; D001713:Biphenyl Compounds / Q000138:chemical synthesis*; D017611:Fluorine Compounds / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C476678:(R)-4'-(1-fluoro-1-methyl-2-(propane-2-sulfonylamino)-ethyl)-biphenyl-4-carboxylic acid methylamide; D000577:Amides; D000588:Amines; D000605:Amino Alcohols; D001713:Biphenyl Compounds; D017611:Fluorine Compounds