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

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

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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 in-termediate of baloxavir marboxil with＞99％yield and＞99％ee at a substrate/catalyst molar ratio of 1000.

Asymmetric transfer hydrogenationBaloxavirChiral alcoholEnantioselectivityHeterocyclic diaryl ketoneRhodium(Ⅲ)

Li Wang、Renwei Xiao、Jingyuan Song、Long-Sheng Zheng、Qiwei Lang、Gen-Qiang Chen、Xumu Zhang

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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

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

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

Southern University of Science and Technology(startup fund)深圳市科创委项目Stable Support Plan Program of Shenzhen Natural Science FundKey-Area Research and Development Program of Guangdong ProvinceInnovative Team of Universities in Guangdong Province国家自然科学基金国家自然科学基金深圳市科创委项目

KQTD20150717103157174202009251612220022020B0101880012020KCXTD0162199111322171129JCYJ20210324104202007

2024

10.1002/cjoc.202300487

中国化学(英文版)
中国化学会 上海有机化学研究所

中国化学(英文版)

CSTPCD
影响因子：0.848
ISSN：1001-604X
年,卷(期)：2024.42(1)
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