Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone

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Abstract

We reported the first example of organocatalytic Michael addition of unprotected 3-prochiral oxindoles 1 to 1,4-naphthoquinone. Quinidine derivative (DHQD) 2PYR was found to be able to catalyze this reaction in up to 83% ee, with moderate to excellent yields. This method could be used for the synthesis of enantioenriched 3,3-diaryloxindoles, and the catalytic synthesis of which was unprecedented. © 2012 Yu et al; licensee Beilstein-Institut. License and terms: see end of document.

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Yu, J. S., Zhou, F., Liu, Y. L., & Zhou, J. (2012). Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone. Beilstein Journal of Organic Chemistry, 8, 1360–1365. https://doi.org/10.3762/bjoc.8.157

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