Synthesis of Chiral beta-Borylated Carboxylic Esters via Nickel-Catalyzed Asymmetric Hydrogenation

Han, Zhengyu1; Liu, Gang1; Zhang, Xianghe1; Li, Anqi1; Dong, Xiu-Qin1; Zhang, Xumu1,2

2019-06-07

10.1021/acs.orglett.9b00994

ORGANIC LETTERS   影响因子和分区

1523-7060

1523-7052

The highly efficient Ni-catalyzed asymmetric hydrogenation of beta-boronic ester substituted-alpha,beta-unsaturated carboxylic esters was successfully developed using (S,S)-Ph-BPE as the ligand. A series of chiral beta-borylated carboxylic esters were obtained with high yields (94%-99% yields) and excellent enantioselectivities (89%-99% ee). The gram-scale asymmetric hydrogenation with a low catalyst loading (0.25 mol %) and synthetic transformation of hydrogenation product demonstrated the great synthetic utility of this methodology.

SCI ; IC ; CCR

英语

NI期刊 ; NI论文

通讯

Fundamental Research Funds for and the Central Universities[204201810202]

Chemistry

Chemistry, Organic

WOS:000471212100011

AMER CHEMICAL SOC

CHEMISTRY

Web of Science

1.Wuhan Univ, Coll Chem & Mol Sci, Minist Educ, Key Lab Biomed Polymers,Engn Res Ctr Organosilico, Wuhan 430072, Hubei, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China

Han, Zhengyu,Liu, Gang,Zhang, Xianghe,et al. Synthesis of Chiral beta-Borylated Carboxylic Esters via Nickel-Catalyzed Asymmetric Hydrogenation[J]. ORGANIC LETTERS,2019,21(11):3923-3926.

Han, Zhengyu,Liu, Gang,Zhang, Xianghe,Li, Anqi,Dong, Xiu-Qin,&Zhang, Xumu.(2019).Synthesis of Chiral beta-Borylated Carboxylic Esters via Nickel-Catalyzed Asymmetric Hydrogenation.ORGANIC LETTERS,21(11),3923-3926.

Han, Zhengyu,et al."Synthesis of Chiral beta-Borylated Carboxylic Esters via Nickel-Catalyzed Asymmetric Hydrogenation".ORGANIC LETTERS 21.11(2019):3923-3926.