Organic Letters 2012-11-29

Pentanidium-catalyzed enantioselective α-hydroxylation of oxindoles using molecular oxygen.

Hong Zan, Clayton A White, Lisa M Thomas, Thach Mai, Guideng Li, Zhenming Xu, Jinsong Zhang, Paolo Casali

Index: Org. Lett. 14(18) , 4762-5, (2012)

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Abstract

Pentanidium-catalyzed α-hydroxylation of 3-substituted-2-oxindoles using molecular oxygen has been developed with good yields and enantioselectivities. This reaction does not require an additional reductant such as triethyl phosphite, which was typically added to reduce the peroxide intermediate. The reaction was demonstrated to consist of two-steps: an enantioselective formation of hydroperoxide oxindole and a kinetic resolution of the hydroperoxide oxindole via reduction with enolates generated from the oxindoles.