The ruthenium catalyzed asymmetric hydrogenation of oximes using binap as the chiral ligand

Krasik, Pavel; Alper, Howard

doi:10.1016/s0957-4166(00)82086-8

Cited by 38 publications

(6 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A novel method of catalytic asymmetric hydrogenation of oximes by the use of BINAP-supported ruthenium catalyst ([RuCl(C 6 H 6 )( R )-BINAP]Cl) generated in the reaction of [RuCl 2 (C 6 H 6 )] 2 and BINAP was proposed by Alper (Scheme ). However, a very modest enantiomeric excess was achieved (29%).…”

Section: Drugs Affecting the Central Nervous Systemmentioning

confidence: 99%

Reductive Amination in the Synthesis of Pharmaceuticals

et al. 2019

View full text Add to dashboard Cite

Reductive amination plays a paramount role in pharmaceutical and medicinal chemistry owing to its synthetic merits and the ubiquitous presence of amines among biologically active compounds. It is one of the key approaches to C–N bond construction due to its operational easiness and a wide toolbox of protocols. Recent studies show that at least a quarter of C–N bond-forming reactions in the pharmaceutical industry are performed via reductive amination. This Review concisely compiles information on 71 medical substances that are synthesized by reductive amination. Compounds are grouped according to the principle of action, which includes drugs affecting the central nervous system, drugs affecting the cardiovascular system, anticancer drugs, antibiotics, antiviral and antifungal medicines, drugs affecting the urinary system, drugs affecting the respiratory system, antidiabetic medications, drugs affecting the gastrointestinal tract, and drugs regulating metabolic processes. A general synthetic scheme is provided for each compound, and the description is focused on reductive amination steps. The green chemistry metric of reaction mass efficiency was calculated for all reactions.

show abstract

Section: Drugs Affecting the Central Nervous Systemmentioning

confidence: 99%

Reductive Amination in the Synthesis of Pharmaceuticals

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Unfortunately, while using [Ru(benzene)Cl 2 ] 2 -(R)-BINAP complex, the stereoinduction remains very modest (Scheme 85). 113 Scheme 85. Ruthenium-catalyzed hydrogenation of oximes.…”

Section: Scheme 84 Synthesis Of Sultam By Using Rutheniumcatalystmentioning

confidence: 99%

“…Unfortunately, while using the [Ru(benzene)Cl 2 ] 2 -(R)-BINAP complex, the stereoinduction remains very modest (Scheme 85). 113 In contrast, the Ru−Binap complex performed much better when challenged with N-sulfonylimine derivatives (Scheme 86). 114 Not surprisingly, the complexation of the oxygen atom of the tosyl group to the metal center is a key parameter, promoting efficient stereoselection.…”

Section: Author Contributionsmentioning

confidence: 99%

Metal-Catalyzed Asymmetric Hydrogenation of C═N Bonds

et al. 2020

View full text Add to dashboard Cite

This review recaps the achievements in the field of metal-catalyzed asymmetric direct hydrogenation of nonactivated and activated imines. A summary of the reported catalytic systems with the corresponding reactivity, selectivity, and limitations are given including a discussion about the effects of some reaction conditions on the enantioselectivity of imine hydrogenation. An analysis of proposed imine hydrogenation mechanisms is discussed.

show abstract

“…On the other hand, iridium catalysts have recently shown high enantioselectivity in hydrogenation of quinoxalines and N-arylimines, but only low ee were obtained with N-alkylimines [10]. Oximes and other C@N-X compounds show even a more pronounced variations in their reactivity [11].…”

Section: Introductionmentioning

confidence: 99%