Asymmetric Hydrogenation of Cyclic Ketimines Catalyzed by Iridium(I)-Complexes of BCPM and Its Analog1

Morimoto, Toshiaki; Nakajima, N.; Achiwa, Kazuo

doi:10.1055/s-1995-5072

Cited by 67 publications

(22 citation statements)

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“…[11] There have been only limited reports of imine hydrosilylation employing complexes of Ir, [12] although Ir complexes are known to promote the hydrogenation of imines. [13][14][15][16][17][18][19][20][21][22] The development of catalysts which are efficient for both N-aryl and N-alkyl imine substrates, as well as aldimines and ketimines, remains an important goal for hydrosilylation research.…”

Section: Introductionmentioning

confidence: 99%

Iridium(I)‐Catalysed Tandem Hydrosilylation‐Protodesilylation of Imines

2005

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Section: Introductionmentioning

confidence: 99%

Iridium(I)‐Catalysed Tandem Hydrosilylation‐Protodesilylation of Imines

2005

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“…Many chiral diphosphine ligands that have been studied in asymmetric reactions with other transition metals such as Ru and Rh, or have been applied to the [35]; the application of DIOP* ligand and its derivatives by Zhang and co-workers obtained 85.0% ee for TMI [36]; the application of BCPM and MCCPM ligands, also by Achiwa et al, achieved 91% ee and 90% ee for TMI [37]; the application of BICP ligand by Zhang and co-workers achieved 95% ee for TMI [38]; and the application of BINAP by Achiwa et al obtained up to 86% ee for the isoquinoline-type imines (Scheme 12) [39]. The remarkable success of Xyliphos in industrial applications revealed the great potential of diphosphine ligands based on a ferrocene backbone, which could possibly enhance the air-stability and electron-donating ability of the ligands.…”

Section: Diphosphine Ligands In Ir-based Catalystsmentioning

confidence: 99%

Asymmetric Hydrogenation of Imines

Zhang

2013

Stereoselective Formation of Amines

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Homogeneous catalytic asymmetric hydrogenation has evolved into a significantly useful methodology for the preparation of enantiopure compounds. Significant advances in asymmetric hydrogenation of imines have enabled a straightforward and powerful approach to various chiral amines. An overview of the many variants of the chiral transition metal catalysts, illustrations of synthetic applications, and discussions of emerging and future strategies from a mechanistic perspective are presented.

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“…An ( S , S ) -BDPP Ir(III) hydride complex has shown high reactivity for this reaction and the amine product was obtained with 80% ee [375] . In the presence of BiI 3 as the additive, a neutral (2 S ,4 S ) -BCPM -Ir complex provided the hydrogenation product with 91% ee at − 30 ° C [381] . At 0 ° C, a neutral BICP -Ir complex together with phthalimide as the additive provided 95% ee for the same substrate 3,4 -Hydroisoquinolines have also been studied with Ir catalysts.…”

Section: Acyclic Iminesmentioning

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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Asymmetric Hydrogenation of Cyclic Ketimines Catalyzed by Iridium(I)-Complexes of BCPM and Its Analog1

Cited by 67 publications

References 0 publications

Iridium(I)‐Catalysed Tandem Hydrosilylation‐Protodesilylation of Imines

Iridium(I)‐Catalysed Tandem Hydrosilylation‐Protodesilylation of Imines

Asymmetric Hydrogenation of Imines

Transition Metal‐Catalyzed Homogeneous Asymmetric Hydrogenation

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