Volume 42, Issue 1 pp. 43-47
Concise Report

Rhodium-Catalyzed Asymmetric Transfer Hydrogenation of Heterocyclic Diaryl Ketones: Facile Access to Key Intermediate of Baloxavir

Li Wang

Li Wang

Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Department of Chemistry, and Medi-Pingshan, Southern University of Science and Technology, Shenzhen, Guangdong, 518000 China

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Renwei Xiao

Renwei Xiao

Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Department of Chemistry, and Medi-Pingshan, Southern University of Science and Technology, Shenzhen, Guangdong, 518000 China

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Jingyuan Song

Jingyuan Song

Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Department of Chemistry, and Medi-Pingshan, Southern University of Science and Technology, Shenzhen, Guangdong, 518000 China

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Long-Sheng Zheng

Long-Sheng Zheng

Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Department of Chemistry, and Medi-Pingshan, Southern University of Science and Technology, Shenzhen, Guangdong, 518000 China

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Qiwei Lang

Corresponding Author

Qiwei Lang

Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Department of Chemistry, and Medi-Pingshan, Southern University of Science and Technology, Shenzhen, Guangdong, 518000 China

E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this author
Gen-Qiang Chen

Corresponding Author

Gen-Qiang Chen

Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen, Guangdong, 518000 China

E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this author
Xumu Zhang

Corresponding Author

Xumu Zhang

Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Department of Chemistry, and Medi-Pingshan, Southern University of Science and Technology, Shenzhen, Guangdong, 518000 China

Chemistry and Chemical Engineering Guangdong Laboratory, Shantou, Guangdong, 515031 China

E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this author
First published: 10 September 2023
Citations: 2

Dedicated to the Memory of Professor Xiyan Lu.

Comprehensive Summary

Transition metal-catalyzed asymmetric transfer hydrogenation has been proven 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.image

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