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Issue 43, 2016
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Catalytic enantioselective cascade Michael/cyclization reaction of 3-isothiocyanato oxindoles with exocyclic α,β-unsaturated ketones en route to 3,2′-pyrrolidinyl bispirooxindoles

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Abstract

Cascade Michael/cyclization reactions between 3-isothiocyanato oxindoles and exocyclic α,β-unsaturated ketones are shown to proceed efficiently in the presence of a quinine-derived tertiary amino-squaramide catalyst and furnish 3,2′-pyrrolidinyl bispirooxindoles containing two spiro-quaternary and three contiguous stereocenters as a single diastereomer with excellent enantioselectivities (up to 99 : 1 er).

Graphical abstract: Catalytic enantioselective cascade Michael/cyclization reaction of 3-isothiocyanato oxindoles with exocyclic α,β-unsaturated ketones en route to 3,2′-pyrrolidinyl bispirooxindoles

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Publication details

The article was received on 07 Oct 2016, accepted on 11 Oct 2016 and first published on 11 Oct 2016


Article type: Communication
DOI: 10.1039/C6OB02187E
Citation: Org. Biomol. Chem., 2016,14, 10175-10179
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    Catalytic enantioselective cascade Michael/cyclization reaction of 3-isothiocyanato oxindoles with exocyclic α,β-unsaturated ketones en route to 3,2′-pyrrolidinyl bispirooxindoles

    S. Kayal and S. Mukherjee, Org. Biomol. Chem., 2016, 14, 10175
    DOI: 10.1039/C6OB02187E

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