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3-Bromopenta-2,4-dienylsilane: a useful reagent for the preparation of [3]dendralenes and polycyclic compounds

Abstract : Starting from (-1-trimethylsilyl-3-bromopenta-2,4-diene, a lithium-bromine exchange reaction followed by addition onto carbonyl compounds provided the corresponding dienyl alcohols. A Peterson-type -elimination promoted by a catalytic amount of trimethylsilyl triflate cross-conjugated gave triene systems ([3]dendralene) which rapidly reacted with the appropriate dienophiles to yield tandem intermolecular Diels-Alder cycloadducts.
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https://hal.inrae.fr/hal-02650128
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Submitted on : Friday, May 29, 2020 - 1:15:32 PM
Last modification on : Tuesday, January 11, 2022 - 5:56:24 PM

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Mohammed Rahif, Maryline Roux, Jérôme Thibonnet, Jean-Luc Parrain. 3-Bromopenta-2,4-dienylsilane: a useful reagent for the preparation of [3]dendralenes and polycyclic compounds. Molecular Diversity, Springer Verlag, 2013, 17 (1), pp.49 - 53. ⟨10.1007/s11030-012-9418-6⟩. ⟨hal-02650128⟩

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