PtCl2-catalyzed cycloisomerizations of 5-en-1-yn-3-ol systems.
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.
Harrak
Youssef
Y
Université Pierre et Marie Curie, Laboratoire de Chimie Organique, UMR CNRS 7611, Tour 44-54, case 229, 4, place Jussieu, 75252 Paris 05, France.
Blaszykowski
Christophe
C
Bernard
Matthieu
M
Cariou
Kevin
K
Mainetti
Emily
E
Mouriès
Virginie
V
Dhimane
Anne-Lise
AL
Fensterbank
Louis
L
Malacria
Max
M
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*
D000480:Alkynes; D003521:Cyclopropanes; D007659:Ketones; D017671:Platinum Compounds; C030173:platinum chloride