Asymmetric Stepwise Reductive Amination of Aryl <i>N</i>‐Heteroaryl Ketones with Benzyl Amines via Iridium Catalysis

A one-pot synthesis of fluorinated chiral alcohols from α-bromoarylketones and fluoroalcohols is described. The fluorinated ketone intermediates were formed from α-bromoarylketones with fluoroalcohols as nucleophiles and solvents, which were reduced subsequentially by adding a chiral Ru catalyst and a mixture of formic acid and triethyl amines (FA: TEA = 1.1:1) as hydrogen donor to give 27 examples of fluorinated chiral alcohols in 60-93% yields and 85-98% ee values. Notably, K 3 PO 4 acts as a base in nucleophilic substitution and an additive in reductive step to enhance the reactivity and enantioselectivity, which is crucial for constructing compatible conditions for one-pot process. This one-pot process is also applicable to gram-scale synthesis.

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One‐Pot Construction of Fluorinated Chiral Alcohols via Sequential Substitution/Asymmetric Transfer Hydrogenation of α‐Bromoarylketones and Fluoroalcohols

Zhao

Wang

Huang

et al. 2022

Adv Synth Catal

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Synthesis of Chiral 2‐Oxazolidinones by Ruthenium‐Catalyzed Asymmetric Transfer Hydrogenation of 2‐Oxazolones

Yu,

Chen,

Liu

et al. 2023

Adv Synth Catal

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An asymmetric transfer hydrogenation of 2‐oxazolones in the presence of a chiral diamine ruthenium catalyst with potassium formate as a hydrogen source and potassium carbonate as an additive in 2,2,2‐trifluoroethanol is described. A series of chiral 2‐oxazolidinones were obtained with 29%–95% yields and 86%–>99% ee's. Furthermore, gram‐scale synthesis of chiral 2‐oxazolidinone and its downstream derivatizations demonstrate the practicality of this method.

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Synthesis of Chiral β‐Hydroxy Selenides by Ruthenium‐catalysed Transfer Hydrogenation of α‐Aryl Selenomethyl Ketones

Liu

Chen

et al. 2023

Asian J Org Chem

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A highly efficient transfer hydrogenation of α‐aryl selenomethyl ketones, using readily available chiral diamine‐derived ruthenium complex as a catalyst and a mixture of formic acid and triethylamine as a hydrogen source in dichloromethane under ambient conditions, is described. A wide range of chiral β‐hydroxy selenides was obtained in 90–99% ee values and moderate to good yields. The practicability is also demonstrated by a gram‐scale synthesis and downstream derivatization.

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Asymmetric Stepwise Reductive Amination of Aryl N‐Heteroaryl Ketones with Benzyl Amines via Iridium Catalysis

Cited by 7 publications

References 31 publications

One‐Pot Construction of Fluorinated Chiral Alcohols via Sequential Substitution/Asymmetric Transfer Hydrogenation of α‐Bromoarylketones and Fluoroalcohols

One‐Pot Construction of Fluorinated Chiral Alcohols via Sequential Substitution/Asymmetric Transfer Hydrogenation of α‐Bromoarylketones and Fluoroalcohols

Synthesis of Chiral 2‐Oxazolidinones by Ruthenium‐Catalyzed Asymmetric Transfer Hydrogenation of 2‐Oxazolones

Synthesis of Chiral β‐Hydroxy Selenides by Ruthenium‐catalysed Transfer Hydrogenation of α‐Aryl Selenomethyl Ketones

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