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.