CHROMATOGRAPHIC RESOLUTION OF SOME CYCLIC SULFOXIMIDES DERIVED FROM PROCHIRAL AND CHIRAL SULFOXIDES

Three endocyclic sulfoxmides of the 1-aryl- and 1-alkyl-3-oxo-benzo[d] -isothia (IV)-azole 1-oxide type (l-substituent = 2'-carboxyphenyl, 2' -carbethoxyphenyl, and octyl, respectively) were found to be well reso lved on a chiral phase derived from bovine serum albumin (BSA). Select ivities (alpha) of 1.74, 1.12, and 1.44, respectively, were obtained. The retention behaviour of 1-octyl-3-oxo-benzo[d]isothia(IV)-azole 1-o xide was further investigated in some detail as a function of the mobi le phase composition and the elution order was established from optica lly active material obtained from the enantiopure sulfoxide precursor. An enantiomeric excess of 85.4% was obtained in the cyclocondensation reaction of the octyl-substituted sulfoxide precursor with hydrazoic acid to the corresponding endocyclic sulfoximide. (C) 1995 Wiley-Liss, Inc.