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Rhodium-Catalyzed Asymmetric Transfer Hydrogenation of Heterocyclic Diaryl Ketones: Facile Access to Key Intermediate of Baloxavir
  • +4
  • Li Wang,
  • Renwei Xiao,
  • Jingyuan Song,
  • Long-Sheng Zheng,
  • Qiwei Lang,
  • Gen-Qiang Chen,
  • Xumu Zhang
Li Wang
Southern University of Science and Technology
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Renwei Xiao
Southern University of Science and Technology
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Jingyuan Song
Southern University of Science and Technology
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Long-Sheng Zheng
Southern University of Science and Technology
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Qiwei Lang
Southern University of Science and Technology
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Gen-Qiang Chen
Southern University of Science and Technology
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Xumu Zhang
Southern University of Science and Technology

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Abstract

Transition metal-catalyzed asymmetric transfer hydrogenation has been proved to be a powerful approach for the synthesis of chiral alcohols. Herein, A highly efficient and enantioselective transfer hydrogenation of dibenzoheptaheterocyclic ketones catalyzed by an arene-tethered TsDPEN-based Rh(III) catalyst has been successfully developed, and a variety of dibenzoheptaheterocyclic ketones were reduced by a 1/1 mixture of formic acid and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) with high yields and enantioselectivities. With this method, the asymmetric reduction of 7,8-difluorodibenzo[b,e]thiepin-11(6H)-one has been realized, providing the key intermediate of baloxavir marboxil with >99% yield and >99% ee at a substrate/catalyst molar ratio of 1000.
04 Sep 20231st Revision Received
04 Sep 2023Submission Checks Completed
04 Sep 2023Assigned to Editor
04 Sep 2023Review(s) Completed, Editorial Evaluation Pending
04 Sep 2023Editorial Decision: Accept