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Iridium-catalysed asymmetric allylic alkylation of benzofuran γ-lactones followed by heteroaromatic Cope rearrangement: study of an unusual reaction sequence

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Abstract

The iridium-catalysed asymmetric allylic alkylation of γ-lactones produces an all-carbon quaternary stereocentre substituted by an allyl and a benzofuran. The resulting 1,5-hexadienes were found to be excellent substrates for an unusual heteroaromatic Cope rearrangement. We describe here the first insight into the synthetic outcome of this intriguing reaction sequence.

Graphical abstract: Iridium-catalysed asymmetric allylic alkylation of benzofuran γ-lactones followed by heteroaromatic Cope rearrangement: study of an unusual reaction sequence

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Publication details

The article was received on 27 Feb 2017, accepted on 05 Apr 2017 and first published on 20 Apr 2017


Article type: Communication
DOI: 10.1039/C7CC01529A
Citation: Chem. Commun., 2017, Advance Article
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    Iridium-catalysed asymmetric allylic alkylation of benzofuran γ-lactones followed by heteroaromatic Cope rearrangement: study of an unusual reaction sequence

    M. Bos and E. Riguet, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC01529A

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