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Cobalt-Catalyzed Efficient Convergent Asymmetric Hydrogenation of E/Z-Enamides. | LitMetric

Cobalt-Catalyzed Efficient Convergent Asymmetric Hydrogenation of E/Z-Enamides.

Angew Chem Int Ed Engl

Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, China.

Published: June 2023

AI Article Synopsis

  • An efficient asymmetric hydrogenation process for internal simple enamides has been developed using a diphosphine-cobalt-zinc catalytic system, particularly with the Ph-BPE ligand.
  • High yields and enantioselectivities were achieved for both acyclic and cyclic enamides with various substituent structures.
  • The resulting hydrogenated products are valuable for synthesizing important chiral drugs, and a plausible catalytic mechanism has been proposed based on DFT calculations.

Article Abstract

Using the diphosphine-cobalt-zinc catalytic system, an efficient asymmetric hydrogenation of internal simple enamides has been realized. In particular, the Ph-BPE ligand can achieve convergent asymmetric hydrogenation of E/Z-substrates. High yields and excellent enantioselectivities were obtained for both acyclic and cyclic enamides bearing α-alkyl-β-aryl, α-aryl-β-aryl, and α-aryl-β-alkyl substituents. Hydrogenated products can be applied for the synthesis of useful chiral drugs such as Arfromoterol, Rotigotine, and Norsertraline. In addition, reasonable catalytic mechanism and stereocontrol mode are proposed based on DFT calculations.

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Source
http://dx.doi.org/10.1002/anie.202303488DOI Listing

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