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Asymmetric organocatalytic synthesis of chiral 3,3-disubstituted oxindoles via a 1,6-conjugate addition reaction

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Abstract

A highly efficient synthesis of chiral 3,3-disubstituted oxindoles was developed using a chiral spirocyclic phosphoric acid catalyzed 1,6-conjugate addition reaction of para-quinone methides derived from N-unprotected isatins with indoles. The reaction proceeds under mild reaction conditions to provide indole-containing N-unprotected oxindoles bearing quaternary stereocenters in good yields and with moderate to excellent enantioselectivities (up to 97% ee).

Graphical abstract: Asymmetric organocatalytic synthesis of chiral 3,3-disubstituted oxindoles via a 1,6-conjugate addition reaction

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Publication details

The article was received on 18 May 2018, accepted on 28 Jun 2018 and first published on 28 Jun 2018


Article type: Paper
DOI: 10.1039/C8OB01169A
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Asymmetric organocatalytic synthesis of chiral 3,3-disubstituted oxindoles via a 1,6-conjugate addition reaction

    A. Rahman, Q. Zhou and X. Lin, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01169A

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