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Catalytic Enantioselective Conia-Ene Reaction
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Section:Abstract
An enantioselective intramolecular Conia-ene reaction of β-dicarbonyl compounds and alkynes to afford methylene cyclopentanes is described. The reaction employs a DTBMSegphos-Pd(II)/Yb(III) dual catalyst system that allows for the asymmetric synthesis of all-carbon quaternary centers and generates a product containing an alkene that can be further manipulated.
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This article has been cited by 33 ACS Journal articles (5 most recent appear below).
Enantioselective Cyclizations of Silyloxyenynes Catalyzed by Cationic Metal Phosphine Complexes
Jean-François Brazeau, Suyan Zhang, Ignacio Colomer, Britton K. Corkey, and F. Dean TosteJournal of the American Chemical Society2012 134 (5), 2742-2749Enantioselective Cyclizations of Silyloxyenynes Catalyzed by Cationic Metal Phosphine Complexes
Jean-François Brazeau, Suyan Zhang, Ignacio Colomer, Britton K. Corkey, and F. Dean TosteJournal of the American Chemical Society2012 134 (5), 2742-2749The discovery of complementary methods for enantioselective transition metal-catalyzed cyclization with silyloxyenynes has been accomplished using chiral phosphine ligands. Under palladium catalysis, 1,6-silyloxyenynes bearing a terminal alkyne led to the ...
Palladated Oligophenylene Thioethers: Synthesis and Reactivity toward Isocyanides, Carbon Monoxide, and Alkynes
José Vicente, José Antonio Abad, and Rosa-María López-Nicolás , Peter G. JonesOrganometallics2011 Article ASAPPalladated Oligophenylene Thioethers: Synthesis and Reactivity toward Isocyanides, Carbon Monoxide, and Alkynes
José Vicente, José Antonio Abad, and Rosa-María López-Nicolás , Peter G. JonesOrganometallics2011 Article ASAPPhenylene thioethers XC6H4(SC6H4R-4)-a (a = 2, 4; X = Br, I; R = H, OMe, NO2) react with Pd(dba)2 and 2 equiv of PPh3 or 1 equiv of 2,2′-bipyridine (bpy) to afford trans-[PdBr{C6H4(SC6H4R-4)-a}(PPh3)2] (for example, a = 2, R = H (1)) or cis-[PdI{C6H4(SC6H...
Phosphoramidite Gold(I)-Catalyzed Diastereo- and Enantioselective Synthesis of 3,4-Substituted Pyrrolidines
Ana Z. González, Diego Benitez, Ekaterina Tkatchouk, William A. Goddard, III, and F. Dean TosteJournal of the American Chemical Society2011 133 (14), 5500-5507Phosphoramidite Gold(I)-Catalyzed Diastereo- and Enantioselective Synthesis of 3,4-Substituted Pyrrolidines
Ana Z. González, Diego Benitez, Ekaterina Tkatchouk, William A. Goddard, III, and F. Dean TosteJournal of the American Chemical Society2011 133 (14), 5500-5507In this article the utility of phosphoramidite ligands in enantioselective AuI catalysis was explored in the development of highly diastereo- and enantioselective AuI-catalyzed cycloadditions of allenenes. A AuI-catalyzed synthesis of 3,4-disubstituted ...
Tandem Cyclopropane Ring-Opening/Conia-ene Reactions of 2-Alkynyl Indoles: A [3 + 3] Annulative Route to Tetrahydrocarbazoles
Huck K. Grover, Terry P. Lebold, and Michael A. KerrOrganic Letters2011 13 (2), 220-223Tandem Cyclopropane Ring-Opening/Conia-ene Reactions of 2-Alkynyl Indoles: A [3 + 3] Annulative Route to Tetrahydrocarbazoles
Huck K. Grover, Terry P. Lebold, and Michael A. KerrOrganic Letters2011 13 (2), 220-223A Zn(NTf2)2 catalyzed tandem reaction consisting of a nucelophilic ring opening of 1,1-cyclopropanediesters by 2-alkynyl indoles followed by a Conia-ene ring closure results in the efficient one-step synthesis of tetrahydrocarbazoles. The adducts may be ...
Gold(I)-Catalyzed Intramolecular Tandem Addition/Friedel−Crafts Reactions between Acyclic Enamides and 1-Arylalkynes
Jennifer A. Kozak, Brian O. Patrick, and Gregory R. DakeThe Journal of Organic Chemistry2010 75 (24), 8585-8590Gold(I)-Catalyzed Intramolecular Tandem Addition/Friedel−Crafts Reactions between Acyclic Enamides and 1-Arylalkynes
Jennifer A. Kozak, Brian O. Patrick, and Gregory R. DakeThe Journal of Organic Chemistry2010 75 (24), 8585-8590Electron-deficient acyclic enamine derivatives react with electron-rich 1-arylalkynes using cationic gold(I) species as catalysts in an intramolecular process to form annulated 1-amido-substituted indene derivatives as the major products. Yields for this ...
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History
- Published In Issue December 14, 2005
- Received July 26, 2005
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