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Issue 3, 2017
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Asymmetric synthesis of trifluoromethyl-substituted 3,3′-pyrrolidinyl-dispirooxindoles through organocatalytic 1,3-dipolar cycloaddition reactions

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Abstract

Unprecedented asymmetric exo′-selective [3 + 2] cycloaddition reactions of CF3-containing isatin-derived azomethine ylides with methyleneindolinones have been disclosed. Under bifunctional organocatalysis by cinchona-derived squaramide catalysts, a series of potential biologically important trifluoromethylated 3,3′-pyrrolidinyl-dispirooxindoles were efficiently constructed in a highly stereoselective manner (84%–99% yields, up to >20 : 1 dr and >99% ee). The reaction leads to the formation of four contiguous stereogenic centers, including two adjacent spiro quaternary stereocenters.

Graphical abstract: Asymmetric synthesis of trifluoromethyl-substituted 3,3′-pyrrolidinyl-dispirooxindoles through organocatalytic 1,3-dipolar cycloaddition reactions

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Publication details

The article was received on 18 Nov 2016, accepted on 22 Dec 2016 and first published on 26 Dec 2016


Article type: Research Article
DOI: 10.1039/C6QO00723F
Org. Chem. Front., 2017,4, 472-482

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    Asymmetric synthesis of trifluoromethyl-substituted 3,3′-pyrrolidinyl-dispirooxindoles through organocatalytic 1,3-dipolar cycloaddition reactions

    W. Huang, Q. Chen, N. Lin, X. Long, W. Pan, Y. Xiong, J. Weng and G. Lu, Org. Chem. Front., 2017, 4, 472
    DOI: 10.1039/C6QO00723F

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