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Issue 4, 2015
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N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes

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Abstract

N-Heterocyclic carbene catalysed redox isomerisation with reduction about the carbonyl has been developed in the transformation of trienyl esters to tetrasubstituted benzaldehydes. The reaction proceeds in good to excellent yield, and in cases that provide 2,2′-biaryls, enantioselectivity is observed. Mechanistic studies demonstrate the intermediacy of a cyclohexenyl β-lactone, while implicating formation of the homoenolate as turnover limiting.

Graphical abstract: N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes

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Publication details

The article was received on 02 Dec 2014, accepted on 22 Jan 2015 and first published on 26 Jan 2015


Article type: Edge Article
DOI: 10.1039/C4SC03726J
Citation: Chem. Sci., 2015,6, 2366-2370
  • Open access: Creative Commons BY-NC license
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    N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes

    L. Candish, A. Levens and D. W. Lupton, Chem. Sci., 2015, 6, 2366
    DOI: 10.1039/C4SC03726J

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