Design and synthesis of novel 1,3-diene bridged chiral atropoisomeric diphosphine ligands for asymmetric hydrogenation of a-dehydro amino ketones

Tan, Xuefeng1,3; Gao, Shuang1; Yang, Chunyan1; Lang, Qiwei1; Ding, Xiaobing1; Chen, Gen-Qiang2; Zhang, Xumu1

2023-09-01

10.1007/s11426-023-1798-1

SCIENCE CHINA-CHEMISTRY   影响因子和分区

1674-7291

1869-1870

A series of novel atropisomeric diphosphine ligands termed TanPhos were designed and synthesized, which has a smaller bite angle compared with that of other ligands such as BINAP. TanPhos showed high reactivity and enantioselectivity in the rhodium-catalyzed asymmetric hydrogenation of a-dehydro amino ketones, and up 99% yield and 99% ee were obtained for a wide range of chiral & alpha;-amino ketones.

diphosphine asymmetric hydrogenation chiral ligand

SCI ; EI

英语

第一 ; 通讯

National Key R&D Program of China[2021YFA1500201] ; Stable Support Plan Program of Shenzhen Natural Science Fund[20200925161222002] ; Key-Area Research and Development Program of Guangdong Province[2020B010188001] ; Innovative Team of Universities in Guangdong Province[2020KCXTD016] ; National Natural Science Foundation of China["21991113","22171129"] ; Guangdong Basic and Applied Basic Research Foundation[2022B1515020055] ; Shenzhen Science and Technology Innovation Committee[JCYJ20210324104202007]

Chemistry

Chemistry, Multidisciplinary

WOS:001068479600001

SCIENCE PRESS

20233914780100

Chelation ; Hydrogenation ; Ligands

Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Organic Compounds:804.1

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, 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.City Univ Hong Kong, Dept Chem, Hong Kong 999077, Peoples R China

Tan, Xuefeng,Gao, Shuang,Yang, Chunyan,et al. Design and synthesis of novel 1,3-diene bridged chiral atropoisomeric diphosphine ligands for asymmetric hydrogenation of a-dehydro amino ketones[J]. SCIENCE CHINA-CHEMISTRY,2023,66(10):2847-2851.

Tan, Xuefeng.,Gao, Shuang.,Yang, Chunyan.,Lang, Qiwei.,Ding, Xiaobing.,...&Zhang, Xumu.(2023).Design and synthesis of novel 1,3-diene bridged chiral atropoisomeric diphosphine ligands for asymmetric hydrogenation of a-dehydro amino ketones.SCIENCE CHINA-CHEMISTRY,66(10),2847-2851.

Tan, Xuefeng,et al."Design and synthesis of novel 1,3-diene bridged chiral atropoisomeric diphosphine ligands for asymmetric hydrogenation of a-dehydro amino ketones".SCIENCE CHINA-CHEMISTRY 66.10(2023):2847-2851.