Rhenium-Catalyzed Regio- and Stereoselective Addition of Two Carbon Units to Terminal Alkynes via Carbon–Carbon Bond Cleavage of β-Keto Sulfones
- 9 May 2011
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 13 (11) , 2959-2961
Abstract
Treatment of β-keto sulfones with terminal alkynes gave unsaturated δ-keto sulfones in good to excellent yields under rhenium catalysis. In this reaction, the insertion of the alkynes into the nonstrained carbon–carbon single bond between the α- and β-positions of the β-keto sulfones proceeded smoothly, and (Z)-isomers were produced with high regio- and stereoselectivities.Keywords
This publication has 19 references indexed in Scilit:
- Nickel-catalysed intramolecular alkene insertion into cyclobutanonesChemical Communications, 2006
- Nickel-Catalyzed Intermolecular Alkyne Insertion into CyclobutanonesJournal of the American Chemical Society, 2005
- Ru‐ and Rh‐Catalyzed C-C Bond Cleavage of Cyclobutenones: Reconstructive and Selective Synthesis of 2‐Pyranones, Cyclopentenes, and CyclohexenonesAngewandte Chemie International Edition, 2004
- Ruthenium-Catalyzed Reconstructive Synthesis of Cyclopentenones by Unusual Coupling of Cyclobutenediones with Alkenes Involving Carbon−Carbon Bond CleavageJournal of the American Chemical Society, 2000
- Reaction of cyclobutenones with low-valent metal reagents to form .eta.4- and .eta.2-vinylketene complexes. Reaction of .eta.4-vinylketene complexes with alkynes to form phenolsOrganometallics, 1992
- Nickel(0)-catalyzed synthesis of substituted phenols from cyclobutenones and alkynesJournal of the American Chemical Society, 1991
- The development of an organotransition metal synthesis of quinonesTetrahedron, 1985
- A simple route to metalla-2-indane-1,3-dionesJournal of Organometallic Chemistry, 1980
- Ring opening of cyclobutenedione derivatives with zerovalent platinumJournal of the Chemical Society, Chemical Communications, 1974
- Nickel(0)-catalyzed reaction of methylenecyclopropanes with olefins. A novel [.sigma.2 + .pi.2] cycloadditionJournal of the American Chemical Society, 1970