Syntheses of alpha-fluoro-alpha,beta-unsaturated thioamides and thiazolines from a fluorophosphonodithioacetate.
A high-yielding synthesis of methyl fluoro(diethoxyphosphono)dithioacetate starting from its difluorinated analogue is reported. Fluorophosphonothioacetamides and -methylthiazolines, prepared from this new dithioester, have been successfully transformed into highly functionalized fluoroalkenes. Good stereoselectivity in favor of the E isomer was observed from the fluorophosphonomethylthiazolines. The potential of these new fluorinated olefinating reagents for the synthesis of modified peptides and glycosides is also disclosed.
Pfund
Emmanuel
E
Laboratoire de Chimie Moléculaire et Thioorganique UMR CNRS 6507, ENSICAEN-Université de Caen 6 Bd du Maréchal Juin, F14050 Caen Cedex, France.
Masson
Serge
S
Vazeux
Michel
M
Lequeux
Thierry
T
D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis*; D013854:Thioamides / Q000138:chemical synthesis*
D006027:Glycosides; D006845:Hydrocarbons, Fluorinated; D007202:Indicators and Reagents; D010455:Peptides; D013844:Thiazoles; D013854:Thioamides