4.8 Article

Pentanidium-Catalyzed Enantioselective α-Hydroxylation of Oxindoles Using Molecular Oxygen

Journal

ORGANIC LETTERS
Volume 14, Issue 18, Pages 4762-4765

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol302030v

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Funding

  1. ARF from NUS [R-143-000-461-112]
  2. National Natural Science Foundation of China [21072044]

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Pentanidium-catalyzed alpha-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 hydroperoxicle oxindole via reduction with enolates generated from the oxindoles.

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