Journal
TETRAHEDRON
Volume 71, Issue 29, Pages 4810-4816Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.05.036
Keywords
Titanium; Hydrobenzoin; Sulfoxide; X-ray diffraction; CD spectra
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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. (C) 2015 Elsevier Ltd. All rights reserved,
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