Ruthenium-catalyzed cycloisomerization of cis-3-en-1-ynes to cyclopentadiene and related derivatives through a 1,5-sigmatropic hydrogen shift of ruthenium-vinylidene intermediates.
We report a new ruthenium-catalyzed cycloisomerization of unactivated cis-3-en-1-ynes, which produces substituted cyclopentadiene and related derivatives. The mechanism of this cyclization is proposed to involve a [1,5]-sigmatropic hydrogen shift of ruthenium-vinylidene intermediates on the basis of deuterium-labeling experiments.
Datta
Swarup
S
Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC.
Odedra
Arjan
A
Liu
Rai-Shung
RS
D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis*; D006859:Hydrogen / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D000480:Alkynes; D003517:Cyclopentanes; D009942:Organometallic Compounds; D014753:Vinyl Compounds; D012428:Ruthenium; D006859:Hydrogen