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Enantioselective intermolecular all-carbon [4+2] annulation via N-heterocyclic carbene organocatalysis

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Abstract

The highly stereoselective intermolecular all-carbon [4+2] annulation between in situ generated acyclic dienolates and α,β-unsaturated acyl azoliums is disclosed. The identification of 2-acyloxy-3-butenones as suitable diene precursors is the key to the success of this transformation. The corresponding highly functionalized cyclohexene products, which are inaccessible from Diels–Alder reactions, were delivered with high levels of diastereo- and enantioselectivities. A series of further transformations based on the product showed the potential of this reaction.

Graphical abstract: Enantioselective intermolecular all-carbon [4+2] annulation via N-heterocyclic carbene organocatalysis

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Publication details

The article was received on 11 Nov 2017, accepted on 23 Nov 2017 and first published on 23 Nov 2017


Article type: Communication
DOI: 10.1039/C7CC08680F
Citation: Chem. Commun., 2017, Advance Article
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    Enantioselective intermolecular all-carbon [4+2] annulation via N-heterocyclic carbene organocatalysis

    G. Zhang, W. Xu, J. Liu, D. K. Das, S. Yang, S. Perveen, H. Zhang, X. Li and X. Fang, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC08680F

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