Catalytic Regio- and Enantioselective Remote Hydrocarboxylation of Unactivated Alkenes with CO₂

Zhou, Li1; Li, Liping2,3; Zhang, Sudong2,3; Kuang, Xiao-kang2,3; Zhou, You-Yun2,3; Tang, Yong1,2,3

2024-07-01

10.1021/jacs.4c05217

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   影响因子和分区

0002-7863

1520-5126

The catalytic regio- and enantioselective hydrocarboxylation of alkenes with carbon dioxide is a straightforward strategy to construct enantioenriched alpha-chiral carboxylic acids but remains a big challenge. Herein we report the first example of catalytic highly enantio- and site-selective remote hydrocarboxylation of a wide range of readily available unactivated alkenes with abundant and renewable CO2 under mild conditions enabled by the SaBOX/Ni catalyst. The key to this success is utilizing the chiral SaBOX ligand, which combines with nickel to simultaneously control both chain-walking and the enantioselectivity of carboxylation. This process directly furnishes a range of different alkyl-chain-substituted or benzo-fused alpha-chiral carboxylic acids bearing various functional groups in high yields and regio- and enantioselectivities. Furthermore, the synthetic utility of this methodology was demonstrated by the concise synthesis of the antiplatelet aggregation drug (R)-indobufen from commercial starting materials.

SCI ; EI

英语

通讯

Southern University of Science and Technology, Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]

Chemistry

Chemistry, Multidisciplinary

WOS:001261325100001

AMER CHEMICAL SOC

Web of Science

1.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
3.Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China

Zhou, Li,Li, Liping,Zhang, Sudong,et al. Catalytic Regio- and Enantioselective Remote Hydrocarboxylation of Unactivated Alkenes with CO₂[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2024.

Zhou, Li,Li, Liping,Zhang, Sudong,Kuang, Xiao-kang,Zhou, You-Yun,&Tang, Yong.(2024).Catalytic Regio- and Enantioselective Remote Hydrocarboxylation of Unactivated Alkenes with CO₂.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY.

Zhou, Li,et al."Catalytic Regio- and Enantioselective Remote Hydrocarboxylation of Unactivated Alkenes with CO₂".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2024).