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Synthesis of substituted 1,3-diene synthetic equivalents by a Ru-catalyzed diyne hydrative cyclization.
Chem Asian J. 2006 Sep 18; 1(3):469-78.CA

Abstract

Catalyzed by [CpRu(CH3CN)3]PF6, the hydrative cyclization of dipropargylic sulfone substrates provides an effective way to synthesize highly functionalized substituted 3-sulfolenes. The amount of water is crucial for the reactivity of this cycloisomerization reaction. The scope and limitations of the Ru-catalyzed cycloisomerization are discussed. A marked ketone-directing effect was observed for the first time in ruthenium-catalyzed cyclizations. A plausible mechanism for the ketone-directed cycloisomerization is also rationalized. The utility of this method was demonstrated by both sulfur dioxide extrusion of the 3-sulfolenes to afford 1,3-dienes and subsequent inter- or intramolecular Diels-Alder reactions.

Authors+Show Affiliations

Trost BM
Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA. bmtrost@stanford.edu
Huang X
No affiliation info available

MeSH

AlkenesAlkynesCarbonCatalysisChemistry, OrganicCyclizationKetonesModels, ChemicalOrganometallic CompoundsRutheniumSulfonesSulfur Dioxide

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

17441084

Citation

Trost, Barry M., and Xiaojun Huang. "Synthesis of Substituted 1,3-diene Synthetic Equivalents By a Ru-catalyzed Diyne Hydrative Cyclization." Chemistry, an Asian Journal, vol. 1, no. 3, 2006, pp. 469-78.
Trost BM, Huang X. Synthesis of substituted 1,3-diene synthetic equivalents by a Ru-catalyzed diyne hydrative cyclization. Chem Asian J. 2006;1(3):469-78.
Trost, B. M., & Huang, X. (2006). Synthesis of substituted 1,3-diene synthetic equivalents by a Ru-catalyzed diyne hydrative cyclization. Chemistry, an Asian Journal, 1(3), 469-78.
Trost BM, Huang X. Synthesis of Substituted 1,3-diene Synthetic Equivalents By a Ru-catalyzed Diyne Hydrative Cyclization. Chem Asian J. 2006 Sep 18;1(3):469-78. PubMed PMID: 17441084.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of substituted 1,3-diene synthetic equivalents by a Ru-catalyzed diyne hydrative cyclization. AU - Trost,Barry M, AU - Huang,Xiaojun, PY - 2007/4/19/pubmed PY - 2007/5/30/medline PY - 2007/4/19/entrez SP - 469 EP - 78 JF - Chemistry, an Asian journal JO - Chem Asian J VL - 1 IS - 3 N2 - Catalyzed by [CpRu(CH3CN)3]PF6, the hydrative cyclization of dipropargylic sulfone substrates provides an effective way to synthesize highly functionalized substituted 3-sulfolenes. The amount of water is crucial for the reactivity of this cycloisomerization reaction. The scope and limitations of the Ru-catalyzed cycloisomerization are discussed. A marked ketone-directing effect was observed for the first time in ruthenium-catalyzed cyclizations. A plausible mechanism for the ketone-directed cycloisomerization is also rationalized. The utility of this method was demonstrated by both sulfur dioxide extrusion of the 3-sulfolenes to afford 1,3-dienes and subsequent inter- or intramolecular Diels-Alder reactions. SN - 1861-471X UR - https://www.unboundmedicine.com/medline/citation/17441084/Synthesis_of_substituted_13_diene_synthetic_equivalents_by_a_Ru_catalyzed_diyne_hydrative_cyclization_ L2 - https://doi.org/10.1002/asia.200600109 DB - PRIME DP - Unbound Medicine ER -