Synthesis of Thiazolines Linked to a Difluoromethylphosphonate Diester via Dithioester Chemistry

A two-step, high-yielding synthesis of Δ2-thiazolines containing a difluoromethylphosphonate diester moiety has been devised using a building block approach. Racemic or chiral β-amino alcohols and diols were coupled with methyl difluoro(diethoxyphosphono)dithioacetate to give predominantly the corresponding β-hydroxythioamides, which were then cyclized to provide a series of novel substituted Δ2-thiazolines.