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Issue 8, 2017
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Decarboxylative Umpolung of conjugated enals to β-carbanions for intramolecular nucleophilic addition to an aldehyde

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Abstract

An interesting Umpolung strategy to generate β-carbanion equivalents from a conjugated enal has been developed. The enal group of compounds 7 was chemospecifically converted to a delocalized carbanion by decarboxylation of the in situ formed imine between the enal and 2,2-diphenylglycine (2), which then underwent nucleophilic addition at the β position of the enal to an intramolecular aldehyde group to give cyclized products 8 in 54–93% yields.

Graphical abstract: Decarboxylative Umpolung of conjugated enals to β-carbanions for intramolecular nucleophilic addition to an aldehyde

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Publication details

The article was received on 23 Dec 2016, accepted on 24 Apr 2017 and first published on 09 May 2017


Article type: Research Article
DOI: 10.1039/C6QO00846A
Citation: Org. Chem. Front., 2017,4, 1586-1589
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    Decarboxylative Umpolung of conjugated enals to β-carbanions for intramolecular nucleophilic addition to an aldehyde

    F. Liu, J. Tian, Y. Liu, C. Tao, H. Zhu, A. Zhang, D. Xu and B. Zhao, Org. Chem. Front., 2017, 4, 1586
    DOI: 10.1039/C6QO00846A

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