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A binary hybrid system comprising a hypervalent iodine(III) reagent and BF 3 •OEt 2  Lewis acid was found to be effective for the diastereoselective α-acetoxylation of cyclic ketones. In this hybrid system, BF 3 •OEt 2  Lewis acid allowed the activation of the hypervalent iodine(III) reagent and cyclic ketones for smooth α-acetoxylation reaction, achieving high diastereoselectivity. This hypervalent iodine-mediated α-acetoxylation of the cyclic ketone reaction plausibly undergoes an S N 2 substitution mechanism via an α- C -bound hypervalent iodine intermediate. The diastereoselectivity of the reaction mainly originates from thermodynamic control.

Hypervalent Iodine-Mediated Diastereoselective α-Acetoxylation of Cyclic Ketones