Asymmetric Sulfoxidation Detail

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Sn2

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

Note: For clarity, the following simplifications were made: (i) dimethyl tartate was used instead of diethyl tartate; (ii) Hünig's base 3a was replaced by trimethylamine; (iii) cumene hydroperoxide was replaced by methyl hydroperoxide; and (iv) the isopropoxide ligand was replaced by a methoxide ligand.

The dimethyl tartate and trimethyl amine ligands coordinate to the titanium atom along with methyl peroxide to form a complex. The NH group of the methyl imidazole forms a hydrogen bond with an O atom of the dimethyl tartate, holding the molecules in a conformation where they can react stereoselectively.

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M. Seenivasaperumal, H.-J. Federsel and K. J. Szabó, Adv. Synth. Catal., 2009, 351, 903–919.