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Iridium-Catalyzed Enantioselective Hydrogenation of α,β-Unsaturated Carboxylic Acids
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Abstract
A highly efficient iridium-catalyzed hydrogenation of α,β-unsaturated carboxylic acids has been developed by using chiral spiro-phosphino-oxazoline ligands, affording α-substituted chiral carboxylic acids in exceptionally high enantioselectivities and reactivities.
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This article has been cited by 5 ACS Journal articles (5 most recent appear below).
Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions of Enantiomerically Enriched Potassium β-Trifluoroboratoamides with Various Aryl- and Hetaryl Chlorides
Gary A. Molander, Inji Shin, and Ludivine Jean-GérardOrganic Letters2010 12 (19), 4384-4387Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions of Enantiomerically Enriched Potassium β-Trifluoroboratoamides with Various Aryl- and Hetaryl Chlorides
Gary A. Molander, Inji Shin, and Ludivine Jean-GérardOrganic Letters2010 12 (19), 4384-4387Enantiomerically enriched potassium β-trifluoroboratoamides were synthesized as air-stable solids in greater than 95:5 dr using pseudoephedrine as the chiral auxiliary. With these chiral nucleophiles, Suzuki−Miyaura cross-coupling reactions were carried ...
Enantioselective Hydrogenation of α-Aryloxy and α-Alkoxy α,β-Unsaturated Carboxylic Acids Catalyzed by Chiral Spiro Iridium/Phosphino-Oxazoline Complexes
Shen Li, Shou-Fei Zhu, Jian-Hua Xie, Song Song, Can-Ming Zhang and Qi-Lin ZhouJournal of the American Chemical Society2010 132 (3), 1172-1179Enantioselective Hydrogenation of α-Aryloxy and α-Alkoxy α,β-Unsaturated Carboxylic Acids Catalyzed by Chiral Spiro Iridium/Phosphino-Oxazoline Complexes
Shen Li, Shou-Fei Zhu, Jian-Hua Xie, Song Song, Can-Ming Zhang and Qi-Lin ZhouJournal of the American Chemical Society2010 132 (3), 1172-1179The iridium-catalyzed highly enantioselective hydrogenation of α-aryloxy and α-alkoxy-substituted α,β-unsaturated carboxylic acids was developed. By using chiral spiro phosphino-oxazoline ligands, the hydrogenation proceeded smoothly to produce various α-...
Enantioselective Intramolecular Oxidative Aminocarbonylation of Alkenylureas Catalyzed by Palladium−Spiro Bis(isoxazoline) Complexes
Tetsuya Tsujihara, Toshio Shinohara, Kazuhiro Takenaka, Shinobu Takizawa, Kiyotaka Onitsuka, Minoru Hatanaka and Hiroaki SasaiThe Journal of Organic Chemistry2009 74 (24), 9274-9279Enantioselective Intramolecular Oxidative Aminocarbonylation of Alkenylureas Catalyzed by Palladium−Spiro Bis(isoxazoline) Complexes
Tetsuya Tsujihara, Toshio Shinohara, Kazuhiro Takenaka, Shinobu Takizawa, Kiyotaka Onitsuka, Minoru Hatanaka and Hiroaki SasaiThe Journal of Organic Chemistry2009 74 (24), 9274-9279An enantioselective synthesis of tetrahydropyrrolo[1,2-c]pyrimidine-1,3-diones via a palladium-catalyzed intramolecular oxidative aminocarbonylation is described. The carbon−carbon double bond of alkenylurea substrates has been shown to react ...
Palladium(II), Platinum(II), and Iridium(I) Complexes of 2-Phosphino-1-dimethylaminoferrocenes: A Survey of Structure and Catalysis
Costa Metallinos, Josh Zaifman, Lori Van Belle, Laura Dodge and Melanie PilkingtonOrganometallics2009 28 (15), 4534-4543Palladium(II), Platinum(II), and Iridium(I) Complexes of 2-Phosphino-1-dimethylaminoferrocenes: A Survey of Structure and Catalysis
Costa Metallinos, Josh Zaifman, Lori Van Belle, Laura Dodge and Melanie PilkingtonOrganometallics2009 28 (15), 4534-4543A series of PdCl2, PtCl2, and Ir(COD)BArF complexes bearing a rare class of racemic bidentate 2-phosphino-1-dimethylaminoferrocene ligands were prepared and characterized by NMR spectroscopy and X-ray crystallography. The new complexes displayed a ...
Iridium-Catalyzed Asymmetric Hydrogenation Yielding Chiral Diarylmethines with Weakly Coordinating or Noncoordinating Substituents
Päivi Tolstoy, Mattias Engman, Alexander Paptchikhine, Jonas Bergquist, Tamara L. Church, Abby W.-M. Leung and Pher G. AnderssonJournal of the American Chemical Society2009 131 (25), 8855-8860Iridium-Catalyzed Asymmetric Hydrogenation Yielding Chiral Diarylmethines with Weakly Coordinating or Noncoordinating Substituents
Päivi Tolstoy, Mattias Engman, Alexander Paptchikhine, Jonas Bergquist, Tamara L. Church, Abby W.-M. Leung and Pher G. AnderssonJournal of the American Chemical Society2009 131 (25), 8855-8860Diarylmethine-containing stereocenters are present in pharmaceuticals and natural products, making the synthetic methods that form these chiral centers are important in industry. We have applied iridium complexes with novel N,P-chelating ligands to the ...
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History
- Published In Issue July 09, 2008
- Article ASAPJune 12, 2008
- Received: April 02, 2008
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