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A Study of Factors Affecting Enantioselectivity in the Oxidation of Aryl Benzyl Sulfides in the Presence of Chiral Titanium Catalysts
Author(s) -
Capozzi Maria Annunziata M.,
Centrone Caterina,
Fracchiolla Giuseppe,
Naso Francesco,
Cardellicchio Cosimo
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100310
Subject(s) - chemistry , aryl , enantiopure drug , enantioselective synthesis , catalysis , titanium , sulfoxide , organic chemistry , combinatorial chemistry , alkyl
A series of experiments was performed to test a theoretical model that we have recently proposed to explain the highly enantioselective oxidation of aryl benzyl sulfides with tert ‐butyl hydroperoxide in the presence of a complex between titanium and ( S , S )‐ or ( R , R )‐hydrobenzoin. The studied variations involved the sulfides, the ligands, and the order of addition of reactants. The reaction path predicted by our model was confirmed in every experiment. In particular, aryl benzyl sulfides behaved as the ideal substrate for this type of asymmetric oxidation, which yields synthetically useful, enantiopure aryl benzyl sulfoxides in a straightforward manner.