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Chromatographic resolution of some cyclic sulfoximides derived from prochiral and chiral sulfoxides
Author(s) -
Allenmark Stig,
Andersson Christina,
Widell Petra
Publication year - 1995
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530070708
Subject(s) - chemistry , sulfoxide , enantiopure drug , enantiomer , aryl , bovine serum albumin , substituent , enantiomeric excess , elution , alkyl , oxide , resolution (logic) , medicinal chemistry , chromatography , organic chemistry , enantioselective synthesis , catalysis , artificial intelligence , computer science
Abstract Three endocyclic sulfoximides of the 1‐aryl‐ and 1‐alkyl‐3‐oxo‐benzo[ d ]‐isothia (IV)‐azole 1‐oxide type (1‐substituent = 2′‐carboxyphenyl, 2′‐carbethoxyphenyl, and octyl, respectively) were found to be well resolved on a chiral phase derived from bovine serum albumin (BSA). Selectivities (α) 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‐oxide was further investigated in some detail as a function of the mobile phase composition and the elution order was established from optically 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. © 1995 Wiley‐Liss, Inc.