title: 3-Bromopenta-2,4-dienylsilane: a useful reagent for the preparation of [3]dendralenes and polycyclic compounds.
abstract: Starting from (Z)-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 γ-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.
authors: Institut des Sciences Moléculaires de Marseille, Aix-Marseille Université, iSm2-UMR CNRS 6263, Campus scientifique de Saint Jérôme, Service 532, 13397, Marseille Cedex 20, France.
authors: Mohammed
authors: M
authors: Rahif
authors: Maryline
authors: M
authors: Roux
authors: Jérôme
authors: J
authors: Thibonnet
authors: Jean-Luc
authors: JL
authors: Parrain
mesh_terms: D002384:Catalysis; D011083:Polycyclic Compounds / Q000138:chemical synthesis*; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism
chemical_list: D011083:Polycyclic Compounds; D014297:Trimethylsilyl Compounds