Enantioselective synthesis of β-fluoroamines from β-amino alcohols: application to the synthesis of LY503430.
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.
Duthion
Béranger
B
Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
Gomez Pardo
Domingo
D
Cossy
Janine
J
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
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