Chiral Phosphoric Acid Catalyzed Enantioselective Transfer Hydrogenation of <i>ortho</i>‐Hydroxybenzophenone NH Ketimines and Applications

Nguyen, Thanh Binh; Wang, Qian; Guéritte, Françoise

doi:10.1002/chem.201101694

Cited by 51 publications

(13 citation statements)

References 143 publications

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“…Wang et al carried out the enantioselective synthesis of amine 10.4.b by reducing benzhydrylimine with a Hantzsch ester (Scheme ). The yield of 86% and ee of 93% were achieved. Product 10.4.b could be transformed to levocetirizine in a few synthetic steps.…”

Section: Drugs Regulating Metabolic Processesmentioning

confidence: 99%

Reductive Amination in the Synthesis of Pharmaceuticals

et al. 2019

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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.

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Section: Drugs Regulating Metabolic Processesmentioning

confidence: 99%

Reductive Amination in the Synthesis of Pharmaceuticals

et al. 2019

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“…The diastereoselective nucleophilic additions to imines have been applied to the asymmetric synthesis of the chiral amines [45,46]. However, to our knowledge there have been only a few reports on the enantioselective synthesis of -substituted o-hydroxybenzylamines [47,48]. In this paper, we report a catalytic asymmetric hydrogenation of 3-substituted benzisoxazoles to yield chiral -substituted o-hydroxybenzylamines.…”

Section: Open Accessmentioning

confidence: 99%

Catalytic Asymmetric Hydrogenation of 3-Substituted Benzisoxazoles

Ikeda

Kuwano

2012

Molecules

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A variety of 3-substituted benzisoxazoles were reduced with hydrogen using the chiral ruthenium catalyst, {RuCl(p-cymene)[(R,R)-(S,S)-PhTRAP]}Cl. The ruthenium-catalyzed hydrogenation proceeded in high yield in the presence of an acylating agent, affording -substituted o-hydroxybenzylamines with up to 57% ee. In the catalytic transformation, the N-O bond of the benzisoxazole substrate is reductively cleaved by the ruthenium complex under the hydrogenation conditions. The C-N double bond of the resulting imine is saturated stereoselectively through the PhTRAP-ruthenium catalysis. The hydrogenation produces chiral primary amines, which may work as catalytic poisons, however, the amino group of the hydrogenation product is rapidly acylated when the reaction is conducted in the presence of an appropriate acylating agent, such as Boc 2 O or Cbz-OSu.

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“…We hypothesized that the introduction of an ortho hydroxy group in the substrate would not only accelerate the imine formation process by activating the carbonyl group but also stabilize the labile imine intermediate through intramolecular hydrogen bonding . Meanwhile, intramolecular hydrogen bonding or Lewis acid coordination of the generated imine intermediate will make the imine exist exclusively as the E isomer and thus supply a more rigid steric environment that benefits the enantioinduction process (Scheme ) –. To our delight, the ortho ‐hydroxy‐substituted substrate 5 a reacted smoothly and delivered the primary amine 6 a in 85 % yield and 98 % ee .…”

Section: Figurementioning

confidence: 99%

Ruthenium‐Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H₂

Zhang

et al. 2020

Angewandte Chemie

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A Ru‐catalyzed direct asymmetric reductive amination of ortho‐OH‐substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible ‐OH group.

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Chiral Phosphoric Acid Catalyzed Enantioselective Transfer Hydrogenation of ortho‐Hydroxybenzophenone NH Ketimines and Applications

Cited by 51 publications

References 143 publications

Reductive Amination in the Synthesis of Pharmaceuticals

Reductive Amination in the Synthesis of Pharmaceuticals

Catalytic Asymmetric Hydrogenation of 3-Substituted Benzisoxazoles

Ruthenium‐Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H₂

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Chiral Phosphoric Acid Catalyzed Enantioselective Transfer Hydrogenation of ortho‐Hydroxybenzophenone NH Ketimines and Applications

Cited by 51 publications

References 143 publications

Reductive Amination in the Synthesis of Pharmaceuticals

Reductive Amination in the Synthesis of Pharmaceuticals

Catalytic Asymmetric Hydrogenation of 3-Substituted Benzisoxazoles

Ruthenium‐Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2

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Ruthenium‐Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H₂