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Issue 8, 2018
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Organocatalytic Michael/cyclization cascade reactions of 3-isothiocyanato oxindoles with 3-trifluoroethylidene oxindoles: an approach for the synthesis of 3′-trifluoromethyl substituted 3,2′-pyrrolidinyl-bispirooxindoles

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Abstract

An efficient asymmetric Michael/cyclization cascade reaction of 3-isothiocyanato oxindoles with 3-trifluoroethylidene oxindoles has been revealed. Under bifunctional organocatalysis with a cinchona alkaloid derived squaramide catalyst, a series of novel 3′-trifluoromethyl substituted 3,2′-pyrrolidinyl-bispirooxindoles were conveniently constructed in a highly stereoselective manner (up to 96% yield, >20 : 1 dr and >99% ee). The reaction leads to the formation of three contiguous stereogenic centers and two spiro quaternary stereocenters.

Graphical abstract: Organocatalytic Michael/cyclization cascade reactions of 3-isothiocyanato oxindoles with 3-trifluoroethylidene oxindoles: an approach for the synthesis of 3′-trifluoromethyl substituted 3,2′-pyrrolidinyl-bispirooxindoles

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Publication details

The article was received on 15 Jan 2018, accepted on 19 Feb 2018 and first published on 19 Feb 2018


Article type: Research Article
DOI: 10.1039/C8QO00044A
Citation: Org. Chem. Front., 2018,5, 1375-1380
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    Organocatalytic Michael/cyclization cascade reactions of 3-isothiocyanato oxindoles with 3-trifluoroethylidene oxindoles: an approach for the synthesis of 3′-trifluoromethyl substituted 3,2′-pyrrolidinyl-bispirooxindoles

    W. Zhu, Q. Chen, N. Lin, K. Chen, Z. Zhang, G. Fang, J. Weng and G. Lu, Org. Chem. Front., 2018, 5, 1375
    DOI: 10.1039/C8QO00044A

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