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. 2012 Oct 24;134(42):17354-7.
doi: 10.1021/ja305991k. Epub 2012 Oct 12.

A tetradentate ligand for the enantioselective Ti(IV)-promoted oxidation of sulfides to sulfoxides: origin of enantioselectivity

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A tetradentate ligand for the enantioselective Ti(IV)-promoted oxidation of sulfides to sulfoxides: origin of enantioselectivity

Timothy R Newhouse et al. J Am Chem Soc. .

Abstract

A detailed stereomechanistic analysis has led to the design of a new tetradentate ligand for the enantioselective Ti(IV)-catalyzed oxidation of unsymmetrical sulfides to sulfoxides with high selectivity. The pathway of this oxidation and the closely related and long-known Kagan-Modena oxidation have been clarified to identify the likely origin of the enantioselectivity.

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