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Issue 3, 2017
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N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate

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Abstract

The N-heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindole and enals was developed, giving the corresponding spirocyclic oxindole-γ-lactones in good yields with high to excellent diastereo- and enantioselectivities. The challenging aliphatic enals worked effectively using this strategy. The oxidative cross coupling of homoenolate and enolate via single electron transfer was proposed as the key step for the reaction.

Graphical abstract: N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate

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Publication details

The article was received on 15 Sep 2016, accepted on 31 Oct 2016 and first published on 09 Nov 2016


Article type: Edge Article
DOI: 10.1039/C6SC04135C
Citation: Chem. Sci., 2017,8, 1936-1941
  • Open access: Creative Commons BY-NC license
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    N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate

    X. Chen, K. Chen, D. Sun and S. Ye, Chem. Sci., 2017, 8, 1936
    DOI: 10.1039/C6SC04135C

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