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Squaramide-catalyzed asymmetric Michael/cyclization cascade reaction of 3-isothiocyanato oxindoles with chalcones for synthesis of pyrrolidinyl spirooxindoles

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Abstract

A highly efficient method for the construction of pyrrolidinyl spirooxindoles with 3-isothiocyanato oxindoles and chalcones via a Michael/cyclization cascade reaction has been developed by using bifunctional cinchona-derived squaramide organocatalysts. A series of complex pyrrolidinyl spirooxindoles could be obtained in high yields (up to 99%) with excellent diastereo- and enantioselectivities (up to >99 : 1 dr, >99% ee) under mild conditions.

Graphical abstract: Squaramide-catalyzed asymmetric Michael/cyclization cascade reaction of 3-isothiocyanato oxindoles with chalcones for synthesis of pyrrolidinyl spirooxindoles

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Publication details

The article was received on 25 Dec 2016, accepted on 15 Mar 2017 and first published on 16 Mar 2017


Article type: Research Article
DOI: 10.1039/C6QO00852F
Citation: Org. Chem. Front., 2017, Advance Article
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    Squaramide-catalyzed asymmetric Michael/cyclization cascade reaction of 3-isothiocyanato oxindoles with chalcones for synthesis of pyrrolidinyl spirooxindoles

    Y. Lin, L. Liu and D. Du, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C6QO00852F

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