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

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.
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https://hal.univ-reims.fr/hal-02429296
Contributor : Emmanuel Riguet <>
Submitted on : Monday, January 6, 2020 - 3:25:19 PM
Last modification on : Tuesday, January 7, 2020 - 1:50:38 AM

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Maxence Bos, Emmanuel Riguet. Iridium-catalysed asymmetric allylic alkylation of benzofuran γ-lactones followed by heteroaromatic Cope rearrangement: study of an unusual reaction sequence. Chemical Communications, Royal Society of Chemistry, 2017, 53 (36), pp.4997-5000. ⟨10.1039/c7cc01529a⟩. ⟨hal-02429296⟩

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