Reductions of 1,3-dicarbonyl systems with ruthenium-biarylbisphosphine catalysts

Ager, David J.; Laneman, Scott A.

doi:10.1016/s0957-4166(97)00455-2

Cited by 140 publications

(37 citation statements)

References 78 publications

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“…Asymmetric hydrogenation of β -keto esters have been studied in great detail, especially with Ru catalysts [238] . Several Ru -BINAP complexes were proved highly effective for a wide variety of β -keto esters [18a,239] .…”

Section: β -Keto Estersmentioning

confidence: 99%

Transition Metal‐Catalyzed Homogeneous Asymmetric Hydrogenation

Gao

Zhang

2010

Catalytic Asymmetric Synthesis

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INTRODUCTIONAmong all the catalytic asymmetric methodologies to chiral compounds, homogenous transition metal -catalyzed asymmetric hydrogenation plays a particularly important role [1] . Its highly effi cient, environmental friendly, and cost -effective natures have undoubtly made it one of the most studied methodologies during the past 40 years. As a result, the vast number of catalytic systems developed has also had a signifi cant impact on other areas of asymmetric catalysis [2] . More signifi cantly, the achievements from academia research on asymmetric hydrogenation were frequently acknowledged with industrial applications, which, in turn, provide an important driving force for its basic research [3] .Hundreds of catalytic systems have been developed since the seminal discoveries from Knowles and Sabacky [4] , Kagan and Dang [5] , and Horner et al. [6] . In many cases, series of chiral catalysts were developed based on the similar scaffolds and were prepared for the same reactions. Although these analogous ligands are more likely prepared for the purpose of patent protection other than academic curiosity, they indeed provide us an excellent opportunity to compare, evaluate, and study every aspect of the catalysts in asymmetric hydrogenation. In the meantime, a large number of prochiral unsaturated compounds have been successfully hydrogenated with excellent enantioselectivities. Practical applications with very low catalyst loadings and complex substrate structures have continued to emerge since the publication of the last edition of this book.

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Section: β -Keto Estersmentioning

confidence: 99%

Transition Metal‐Catalyzed Homogeneous Asymmetric Hydrogenation

Gao

Zhang

2010

Catalytic Asymmetric Synthesis

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“…An important breakthrough in this area was achieved by Noyori and co-workers using a XylBINAP/DAIPEN/Ru complex (DAIPEN ) 1,1-di(4-anisyl)-2-isopropyl-1,2-ethylenediamine) in conjunction with an inorganic base in 2-propanol in the hydrogenation of an extensive range of unfunctionalized ketones. 21 During the course of our studies to broaden the application scope of P-Phos ligands, we attempted to employ a substantially less expensive chiral diamine, DPEN (1,2-diphenylethylenediamine), instead of the expensive fancy diamine DAIPEN. The preformed complex trans-[RuCl 2 {(R)-Xyl-Phos}{(R,R)-DPEN}] proved to be an extremely versatile catalyst precursor for the asymmetric hydrogenation of a wide spectrum of prochiral ketones.…”

Section: Scheme 3 Hydrogenation Of 2-(6′-methoxy-2′-naphthyl)propenoicmentioning

confidence: 99%

P-Phos: A Family of Versatile and Effective Atropisomeric Dipyridylphosphine Ligands in Asymmetric Catalysis

Chan

2006

Acc. Chem. Res.

121

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This Account outlines our efforts in the design and synthesis of a family of highly effective atropisomeric dipyridylphosphine ligands (P-Phos and its variants) and in the development of their widespread applications in transition-metal-catalyzed asymmetric reactions including hydrogenation, hydrosilylation, and C-C bond formation. Desirable attributes, such as air stability, broad substrate scope, fast rates of reaction, excellent enantioselectivities, low catalyst loading, and mild conditions, make the catalyst systems highly attractive and thus may provide excellent opportunities for practical applications.

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“…We chose to focus on the Ru(BINAP) species developed by Noyori 66 and others, 67 which displays excellent chiral recognition and has demonstrated the ability to catalyze the asymmetric reduction of various -keto esters. 68 We eventually settled on the modified Noyori catalyst [RuCl 2 -(BINAP)] 2 ‚NEt 3 ].…”

Section: Dianion Equivalents Corresponding To the Polypropionate Domamentioning

confidence: 99%

Complex Target-Oriented Synthesis in the Drug Discovery Process: A Case History in the dEpoB Series

1999

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Reductions of 1,3-dicarbonyl systems with ruthenium-biarylbisphosphine catalysts

Cited by 140 publications

References 78 publications

Transition Metal‐Catalyzed Homogeneous Asymmetric Hydrogenation

Transition Metal‐Catalyzed Homogeneous Asymmetric Hydrogenation

P-Phos: A Family of Versatile and Effective Atropisomeric Dipyridylphosphine Ligands in Asymmetric Catalysis

Complex Target-Oriented Synthesis in the Drug Discovery Process: A Case History in the dEpoB Series

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