BUCKLEY, B.R., NEARY, S.P. and ELSEGOOD, M.R.J., 2010. The first enantiomerically pure thiadiazol-3-one 1-oxide and thiatriaza-indene 3-oxide systems chiral at the sulfur atom. Tetrahedron: Asymmetry, 21 (16), pp. 1959 - 1962
The first synthesis of an enantiomerically pure C2 symmetric benzothiadiazole 2-oxide is described along with the first synthesis of an enantiomerically thiadiazol-3-one 1-oxide and a thiatriaza-indene 3-oxide system both chiral at the sulfur atom. Excellent levels of diastereoselectivity were observed in the SO installation step, that is, the reaction of the prerequisite bis-amines with thionyl chloride at ambient temperature.