Optically active 4-aryl-4-trifluoromethyl-4H-1,3-oxa(thia)zines

S(−)-4-Aryl-4-(N-acylamino)-5,5,5-trifluoropentan-2-ones have been reacted with phosphorus pentachloride and pentasulfide to yield S(−)-4-aryl-4-trifluoromethyl-4H-1,3-oxazines and S(+)-4-aryl-4-trifluoromethyl-4H-1,3-thiazines, respectively.

Graphical abstractSynthesis of chiral 4-trifluoromethyl-4H-1,3-oxazines and 4-trifluoromethyl-4H-1,3-thiazines from enantiomerically enriched N-acyl derivatives of 4-amino-4-aryl-5,5,5-trifluoropentan-2-ones is described.Figure optionsDownload full-size imageDownload as PowerPoint slide