Synthesis of thiazolines linked to a difluoromethylphosphonate diester via dithioester chemistry

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.