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Issue 34, 2017
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Asymmetric [3+2] cycloaddition of 3-amino oxindole-based azomethine ylides with α,β-ynones: a straightforward approach to spirooxindoles incorporating 2,5-dihydropyrroles and pyrroles

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Abstract

An organocatalytic asymmetric [3+2] cycloaddition of 3-amino oxindole-based azomethine ylides and α,β-ynones has been developed. This reaction afforded spiro[dihydropyrrole-2,3′-oxindole] products in high chemical yields with excellent stereoselectivities (up to 99% yields, >20 : 1 dr and >99% ee). Notably, a series of important spiro[pyrrole-oxindole] derivatives were readily obtained via oxidation of the cycloadducts, thus extending the diversity of the products.

Graphical abstract: Asymmetric [3+2] cycloaddition of 3-amino oxindole-based azomethine ylides with α,β-ynones: a straightforward approach to spirooxindoles incorporating 2,5-dihydropyrroles and pyrroles

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Publication details

The article was received on 03 Mar 2017, accepted on 31 Mar 2017 and first published on 04 Apr 2017


Article type: Communication
DOI: 10.1039/C7CC01653K
Citation: Chem. Commun., 2017,53, 4714-4717
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    Asymmetric [3+2] cycloaddition of 3-amino oxindole-based azomethine ylides with α,β-ynones: a straightforward approach to spirooxindoles incorporating 2,5-dihydropyrroles and pyrroles

    G. Zhu, S. Wu, X. Bao, L. Cui, Y. Zhang, J. Qu, H. Chen and B. Wang, Chem. Commun., 2017, 53, 4714
    DOI: 10.1039/C7CC01653K

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