Synthesis and stereoselective oxidation of α-thio-β-chloropropenyloxazolidin-2-ones

The investigation of the stereoselective reaction of α-thiopropanoyloxazolidin-2-ones with NCS to yield α-thio-β-chloropropenyloxazolidin-2-ones is described. Diastereoselective sulfur oxidation of the resulting α-thio-β-chloropropenyloxazolidin-2-ones shows modest diastereocontrol. However, via a combination of diastereoselective oxidation and subsequent kinetic resolution in the sulfoxide oxidation, diastereoselectivities of up to 94% de have been achieved.

Figure optionsDownload as PowerPoint slide