Design and Synthesis of Sulfur-Containing Tetradentate Ligands for Ir-Catalyzed Asymmetric Hydrogenation of Ketones

Wang, Yuan-Zheng1; Duan, Ya-Nan4; Chen, Gen-Qiang2,3; Zhang, Xumu1,4

2024-09-01

10.1021/acs.orglett.4c03264

ORGANIC LETTERS   影响因子和分区

1523-7060

1523-7052

Developing highly active and enantioselective ligands for the asymmetric hydrogenation of ketones has consistently attracted significant attention from scientists. A series of novel tetradentate sulfur-containing ligands, termed as f-thiophamidol, were successfully designed and synthesized which exhibited excellent performance in the asymmetric hydrogenation of simple ketones (up to 99% yield, 99% ee) and alpha-substituted beta-keto sulfonamides (up to 99% yield, 99% ee, 99:1 dr). The subsequent successful gram-scale experiments with high TON demonstrated the immense potential application value of this system in synthesizing drug molecules.

SCI

英语

第一 ; 通讯

National Key R&D Program of China[2021YFA1500200] ; National Natural Science Foundation of China["21991113","22171129"] ; Chemistry and Chemical Engineering Guangdong Laboratory["2011006","2132013"] ; Innovative Team of Universities in Guangdong Province[2020KCXTD016] ; Shenzhen Science and Technology Innovation Committee[JCYJ20210324104202007] ; Guangdong Basic and Applied Basic Research Foundation[2022B1515020055]

Chemistry

Chemistry, Organic

WOS:001325638200001

AMER CHEMICAL SOC

Web of Science

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

Wang, Yuan-Zheng,Duan, Ya-Nan,Chen, Gen-Qiang,et al. Design and Synthesis of Sulfur-Containing Tetradentate Ligands for Ir-Catalyzed Asymmetric Hydrogenation of Ketones[J]. ORGANIC LETTERS,2024.

Wang, Yuan-Zheng,Duan, Ya-Nan,Chen, Gen-Qiang,&Zhang, Xumu.(2024).Design and Synthesis of Sulfur-Containing Tetradentate Ligands for Ir-Catalyzed Asymmetric Hydrogenation of Ketones.ORGANIC LETTERS.

Wang, Yuan-Zheng,et al."Design and Synthesis of Sulfur-Containing Tetradentate Ligands for Ir-Catalyzed Asymmetric Hydrogenation of Ketones".ORGANIC LETTERS (2024).