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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.
J Am Chem Soc. 2005 Aug 24; 127(33):11606-7.JA

Abstract

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.

Authors+Show Affiliations

Datta S
Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC.
Odedra A
No affiliation info available
Liu RS
No affiliation info available

MeSH

AlkynesCatalysisCyclizationCyclopentanesHydrogenMolecular StructureOrganometallic CompoundsRutheniumStereoisomerismVinyl Compounds

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16104729

Citation

Datta, Swarup, et al. "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." Journal of the American Chemical Society, vol. 127, no. 33, 2005, pp. 11606-7.
Datta S, Odedra A, Liu RS. 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. J Am Chem Soc. 2005;127(33):11606-7.
Datta, S., Odedra, A., & Liu, R. S. (2005). 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. Journal of the American Chemical Society, 127(33), 11606-7.
Datta S, Odedra A, Liu RS. 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. J Am Chem Soc. 2005 Aug 24;127(33):11606-7. PubMed PMID: 16104729.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 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. AU - Datta,Swarup, AU - Odedra,Arjan, AU - Liu,Rai-Shung, PY - 2005/8/18/pubmed PY - 2005/11/3/medline PY - 2005/8/18/entrez SP - 11606 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 127 IS - 33 N2 - 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. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/16104729/Ruthenium_catalyzed_cycloisomerization_of_cis_3_en_1_ynes_to_cyclopentadiene_and_related_derivatives_through_a_15_sigmatropic_hydrogen_shift_of_ruthenium_vinylidene_intermediates_ DB - PRIME DP - Unbound Medicine ER -