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Effective and diastereoselective preparation of dispiro[cyclopent-3′-ene]bisoxindoles via novel [3 + 2] annulation of isoindigos and MBH carbonates

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Abstract

A novel and diastereoselective [3 + 2] annulation of isoindigos and Morita–Baylis–Hillman carbonates has been developed for the highly efficient and one-step preparation of highly steric dispiro[cyclopent-3′-ene]bisoxindoles with two all-carbon quaternary spirocenters and three adjacent cycles in excellent yields (up to >99%) and diastereoselectivities (up to >20 : 1) under mild conditions within a few minutes. A series of dispiro[cyclopent-3′-ene]bisoxindoles were obtained and scale-up experiment was conducted with excellent results demonstrating the potential applications of this protocol.

Graphical abstract: Effective and diastereoselective preparation of dispiro[cyclopent-3′-ene]bisoxindoles via novel [3 + 2] annulation of isoindigos and MBH carbonates

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Publication details

The article was received on 05 Dec 2017, accepted on 22 Jan 2018 and first published on 22 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB03009F
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Effective and diastereoselective preparation of dispiro[cyclopent-3′-ene]bisoxindoles via novel [3 + 2] annulation of isoindigos and MBH carbonates

    H. Ren, L. Peng, X. Song, L. Liao, Y. Zou, F. Tian and L. Wang, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB03009F

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