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Issue 5, 2018
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Organocatalytic [3 + 2] cycloaddition of oxindole-based azomethine ylides with 3-nitrochromenes: a facile approach to enantioenriched polycyclic spirooxindole-chromane adducts

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Abstract

An organocatalytic asymmetric [3 + 2] cycloaddition of oxindole-based azomethine ylides with 3-nitro-2H-chromenes has been developed. This reaction provides a facile approach to densely functionalized polycyclic spirooxindole-chromane adducts featuring four contiguous stereogenic centers, including two tetrasubstituted carbon centers. The products were obtained in high yields with good to excellent stereoselectivities (up to 99% yields, 96% ee and >20 : 1 dr). In addition, the spiro[pyrrolidine-2,3′-oxindole]-chromane adducts could be readily derivatized via simple oxidation and reduction treatment. A dual activation working model to illuminate the stereochemical course of the [3 + 2] cycloaddition event is proposed.

Graphical abstract: Organocatalytic [3 + 2] cycloaddition of oxindole-based azomethine ylides with 3-nitrochromenes: a facile approach to enantioenriched polycyclic spirooxindole-chromane adducts

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Publication details

The article was received on 09 Dec 2017, accepted on 05 Jan 2018 and first published on 05 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB03051G
Citation: Org. Biomol. Chem., 2018,16, 807-815
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    Organocatalytic [3 + 2] cycloaddition of oxindole-based azomethine ylides with 3-nitrochromenes: a facile approach to enantioenriched polycyclic spirooxindole-chromane adducts

    S. Wu, G. Zhu, S. Wei, H. Chen, J. Qu and B. Wang, Org. Biomol. Chem., 2018, 16, 807
    DOI: 10.1039/C7OB03051G

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