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Investigations on the Iron‐Catalyzed Asymmetric Sulfide Oxidation
Author(s) -
Legros Julien,
Bolm Carsten
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400857
Subject(s) - enantioselective synthesis , sulfoxide , catalysis , sulfide , chemistry , hydrogen peroxide , sulfone , kinetic resolution , carboxylate , salt (chemistry) , organic chemistry , combinatorial chemistry
The development of an enantioselective sulfide oxidation involving a chiral iron catalyst and aqueous hydrogen peroxide as oxidant is described. In the presence of a simple carboxylic acid, or a carboxylate salt, the reaction affords sulfoxides with remarkable enantioselectivities (up to 96 % ee ) in moderate to good yields. The influence of the structure of the additive on the reaction outcome is reported. In the sulfoxide‐to‐sulfone oxidation a kinetic resolution (with s =4.8) occurs, which, however, plays only a negligible role in the overall enantioselective process. Furthermore, a positive nonlinear relationship between the ee of the product and that of the catalyst has been found. On the basis of these observations, a possible catalyst structure is proposed.