Synthesis of thiazolines linked to a difluoromethylphosphonate diester via dithioester chemistry.
[reaction: see text] A two-step, high-yielding synthesis of delta(2)-thiazolines containing a difluoromethylphosphonate diester moiety has been devised using a building block approach. Racemic or chiral beta-amino alcohols and diols were coupled with methyl difluoro(diethoxyphosphono)dithioacetate to give predominantly the corresponding beta-hydroxythioamides, which were then cyclized to provide a series of novel substituted delta(2)-thiazolines.
Pfund
Emmanuel
E
Laboratoire de Chimie Moléculaire et Thio-organique UMR CNRS 6507 ISMRA, UFR Sciences, Université de Caen, 6 Bd Maréchal Juin, 14050 Caen Cedex, France.
Lequeux
Thierry
T
Masson
Serge
S
Vazeux
Michel
M
D000605:Amino Alcohols / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis; D010756:Phosphoric Acids / Q000737:chemistry*; D013844:Thiazoles / Q000737:chemistry*
D000605:Amino Alcohols; D004952:Esters; D009705:Nucleosides; D010756:Phosphoric Acids; D013844:Thiazoles; C081381:difluorophosphoric acid; D005459:Fluorides