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Updated: Jan 15, 2026
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Amine-Borane-Promoted Rhodium-Catalyzed Asymmetric Transfer Hydrogenation of β-Chloro Ketones
Hao Sun1,2, Sai Ruan1, Virginie Ratovelomanana-Vidal3
1Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Department of Chemistry and Medi-X Pingshan, Southern University of Science and Technology, Shenzhen 518055, China.
Abstract:
We report a rhodium-catalyzed asymmetric transfer hydrogenation of β-chloro ketones promoted by amine-boranes. A broad range of substrates was reduced in up to 99% yield and >99% ee, with gram-scale reactions completed within 1 h. The resulting 3-chloroalkanols serve as versatile intermediates for the synthesis of pharmaceuticals such as (S)-Nisoxetine, (S)-Fluoxetine, (S)-Tomoxetine, (S)-Duloxetine, (S)-Dapoxetine, and Ezetimibe analogues. DFT calculations reveal that C-H···π interactions and hydrogen bonding control stereoselectivity, and the effect of different amine-boranes on enantioselectivity was rationalized, providing guidance for broader application in asymmetric transfer hydrogenation.
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