The search for exceptions in the highly enantioselective titanium catalysed oxidation of aryl benzyl sulfides
2015
Capozzi, Maria Annunziata M. | Terraneo, Giancarlo | Cavallo, Gabriella | Cardellicchio, Cosimo
After the discovery of a few cases of lower enantioselectivity in the oxidation of aryl benzyl sulfides with hydroperoxides in the presence of a complex between titanium isopropoxide and (S, S)-hydrobenzoin, a screening of the oxidation of new substrates that are related to the structures that gave low ee values, was performed. From this screening, we confirmed that only a few sulfides remain as exceptions within a framework of exceptionally high stereoselectivity of the oxidation reaction. Moreover, the exceptions are clearly identified and are connected to particular coordinating moieties present on the aryl groups.
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