Enantiodivergent Synthesis of Chiral Tetrahydroquinoline Derivatives via Ir-Catalyzed Asymmetric Hydrogenation: Solvent-Dependent Enantioselective Control and Mechanistic Investigations

Han, Zhengyu1; Liu, Gang1; Yang, Xuanliang1; Dong, Xiu-Qin1,2; Zhang, Xumu3,4

2021-06-18

10.1021/acscatal.1c01353

ACS Catalysis   影响因子和分区

2155-5435

Ir-catalyzed asymmetric hydrogenation of quinolines was developed, and both enantiomers of chiral tetrahydroquinoline derivatives could be easily obtained, respectively, in high yields with good enantioselectivities through the adjustment of reaction solvents (toluene/dioxane: up to 99% yield, 98% ee (R), TON = 680; EtOH: up to 99% yield, 94% ee (S), TON = 1680). It provided an efficient and simple synthetic strategy for the enantiodivergent synthesis of chiral tetrahydroquinolines, and gram-scale asymmetric hydrogenation proceeded well with low-catalyst loading in these two reaction systems. A series of deuterium-labeling experiments, control experiments, and H-1 NMR and electrospray ionization-mass spectrometry experiments have been conducted, and a reasonable and possible reaction process was revealed on the basis of these useful observations.

enantiodivergent synthesis asymmetric catalysis chiral tetrahydroquinolines hydrogenation enantioselectivity

SCI ; EI

英语

通讯

National Natural Science Foundation[22071187] ; Natural Science Foundation of Jiangsu Province[BK20190213] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]

Chemistry

Chemistry, Physical

WOS:000664333800049

AMER CHEMICAL SOC

20212610563319

Catalysis ; Electrospray ionization ; Enantiomers ; Enantioselectivity ; Mass spectrometry ; Organic solvents

Chemistry:801 ; Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Chemical Agents and Basic Industrial Chemicals:803

Web of Science

1.Wuhan Univ, Coll Chem & Mol Sci, Minist Educ, Engn Res Ctr Organosilicon Cpds & Mat, Wuhan 430072, Hubei, Peoples R China
2.Wuhan Univ, Suzhou Inst, Suzhou 215123, Jiangsu, Peoples R China
3.Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Guangdong, Peoples R China
4.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China

Han, Zhengyu,Liu, Gang,Yang, Xuanliang,et al. Enantiodivergent Synthesis of Chiral Tetrahydroquinoline Derivatives via Ir-Catalyzed Asymmetric Hydrogenation: Solvent-Dependent Enantioselective Control and Mechanistic Investigations[J]. ACS Catalysis,2021,11(12):7281-7291.

Han, Zhengyu,Liu, Gang,Yang, Xuanliang,Dong, Xiu-Qin,&Zhang, Xumu.(2021).Enantiodivergent Synthesis of Chiral Tetrahydroquinoline Derivatives via Ir-Catalyzed Asymmetric Hydrogenation: Solvent-Dependent Enantioselective Control and Mechanistic Investigations.ACS Catalysis,11(12),7281-7291.

Han, Zhengyu,et al."Enantiodivergent Synthesis of Chiral Tetrahydroquinoline Derivatives via Ir-Catalyzed Asymmetric Hydrogenation: Solvent-Dependent Enantioselective Control and Mechanistic Investigations".ACS Catalysis 11.12(2021):7281-7291.