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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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Supplementary files

Article information


Submitted
09 Dec 2017
Accepted
05 Jan 2018
First published
05 Jan 2018

Org. Biomol. Chem., 2018,16, 807-815
Article type
Paper

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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