title: PtCl2-catalyzed cycloisomerizations of 5-en-1-yn-3-ol systems.
abstract: 5-En-1-yn-3-ol substrates bearing a free hydroxyl group or an acyl group are highly versatile partners for PtCl2-catalyzed cycloisomerizations. Electrophilic activation of the alkyne moiety triggers at wish a hydride or an O-acyl migration yielding at the end to regioisomeric keto derivatives. The efficient preparation of Sabina ketone, an important monoterpene precursor, has been worked out.
authors.affiliation: Université Pierre et Marie Curie, Laboratoire de Chimie Organique, UMR CNRS 7611, Tour 44-54, case 229, 4, place Jussieu, 75252 Paris 05, France.
authors.forename: Youssef
authors.initials: Y
authors.lastname: Harrak
authors.forename: Christophe
authors.initials: C
authors.lastname: Blaszykowski
authors.forename: Matthieu
authors.initials: M
authors.lastname: Bernard
authors.forename: Kevin
authors.initials: K
authors.lastname: Cariou
authors.forename: Emily
authors.initials: E
authors.lastname: Mainetti
authors.forename: Virginie
authors.initials: V
authors.lastname: Mouriès
authors.forename: Anne-Lise
authors.initials: AL
authors.lastname: Dhimane
authors.forename: Louis
authors.initials: L
authors.lastname: Fensterbank
authors.forename: Max
authors.initials: M
authors.lastname: Malacria
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis; D007536:Isomerism; D007659:Ketones / Q000138:chemical synthesis; D015394:Molecular Structure; D017671:Platinum Compounds / Q000737:chemistry*
chemical_list: D000480:Alkynes; D003521:Cyclopropanes; D007659:Ketones; D017671:Platinum Compounds; C030173:platinum chloride