Hydrogen Bond Enhanced Enantioselectivity in the Nickel-Catalyzed Transfer Hydrogenation of α-Substituted Acrylic Acid with Formic Acid

被引：15
作者：
Sun, Yaxin [1 ]
Wang, Chao [2 ]
Yang, Peng [1 ]
Yue, Jie-Yu [1 ]
Xu, Chang [1 ]
Zhou, Jianrong Steve [4 ]
Tang, Bo [1 ,3 ]
机构：
[1] Shandong Normal Univ, Univ Shandong, Coll Chem Chem Engn & Mat Sci, Minist Educ,Collaborat Innovat Ctr Functionalized, Jinan 250014, Peoples R China
[2] Peking Univ, Lab Computat Chem & Drug Design, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China
[3] Laoshan Lab, Qingdao 266237, Peoples R China
[4] Peking Univ, Sch Chem Biol & Biotechnol, State Key Lab Chem Oncogen, Shenzhen Grad Sch,Guangdong Prov Key Lab Chem Geno, Shenzhen 518055, Peoples R China
来源：
ACS CATALYSIS | 2023年 / 13卷 / 21期
基金：
中国国家自然科学基金; 中国博士后科学基金;
关键词：
nickel; transfer hydrogenation; asymmetrichydrogenation; chiral carboxylic acids; hydrogenbonding; ASYMMETRIC TRANSFER HYDROGENATION; UNSATURATED CARBOXYLIC-ACIDS; C2-SYMMETRICAL BIS(PHOSPHOLANES); PRACTICAL SYNTHESIS; LIGANDS; COMPLEXES; KETONES;
D O I：
10.1021/acscatal.3c04187
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A chiral nickel complex that catalyzed asymmetric transfer hydrogenation of alpha-substituted acrylic acids under mild conditions and avoided the use of high-pressure hydrogen gas was developed. The products included chiral beta-amino acids and alpha-methyl carboxylic acids such as three nonsteroidal anti-inflammatory profens. Deuterium-labeling experiments and DFT studies pointed to an unconventional protonation of a metalacyclopropane complex formed by alpha-phenylacrylic acid which was hydrogen bonded with formic acid. An alternative conventional pathway of nickel hydride insertion cannot explain selective deuteration at beta-position of alpha-phenylacrylic acid when HCO2D was used.
引用
收藏
页码：14213 / 14220
页数：8
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