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

Wang, Li1; Xiao, Renwei1; Song, Jingyuan1; Zheng, Long-Sheng1; Lang, Qiwei1; Chen, Gen-Qiang2; Zhang, Xumu1,3

2023-10-01

10.1002/cjoc.202300487

CHINESE JOURNAL OF CHEMISTRY   Impact Factor & Quartile

1001-604X

1614-7065

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.

Asymmetric transfer hydrogenation Baloxavir Chiral alcohol Enantioselectivity Heterocyclic diaryl ketone Rhodium(III)

SCI

English

First ; Corresponding

Southern University of Science and Technology[JCYJ20210324104202007] ; Shenzhen Science and Technology Innovation Committee[20200925161222002] ; Stable Support Plan Program of Shenzhen Natural Science Fund[2020B010188001] ; Key-Area Research and Development Program of Guangdong Province[2020KCXTD016] ; Innovative Team of Universities in Guangdong Province[22171129]

Chemistry

Chemistry, Multidisciplinary

WOS:001092360900001

WILEY-V C H VERLAG GMBH

CHEMISTRY

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Shenzhen Key Lab Small Mol Drug Discovery & Synth, Shenzhen 518055, Guangdong, Peoples R China
2.Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen 518000, Guangdong, Peoples R China
3.Chem & Chem Engn Guangdong Lab, Shantou 515031, Guangdong, Peoples R China

Wang, Li,Xiao, Renwei,Song, Jingyuan,et al. Rhodium-Catalyzed Asymmetric Transfer Hydrogenation of Heterocyclic Diaryl Ketones: Facile Access to Key Intermediate of Baloxavir[J]. CHINESE JOURNAL OF CHEMISTRY,2023.

Wang, Li.,Xiao, Renwei.,Song, Jingyuan.,Zheng, Long-Sheng.,Lang, Qiwei.,...&Zhang, Xumu.(2023).Rhodium-Catalyzed Asymmetric Transfer Hydrogenation of Heterocyclic Diaryl Ketones: Facile Access to Key Intermediate of Baloxavir.CHINESE JOURNAL OF CHEMISTRY.

Wang, Li,et al."Rhodium-Catalyzed Asymmetric Transfer Hydrogenation of Heterocyclic Diaryl Ketones: Facile Access to Key Intermediate of Baloxavir".CHINESE JOURNAL OF CHEMISTRY (2023).