Citation: LI Yuhan, JIN Rizhe, GAO Lianxun. Synthesis of Chiral Binaphthyl 2,2'-Bipydine and Its Derivatives and Their Application to Asymmetric Synthesis[J]. Chinese Journal of Applied Chemistry, ;2016, 33(7): 792-797. doi: 10.11944/j.issn.1000-0518.2016.07.150353 shu

Synthesis of Chiral Binaphthyl 2,2'-Bipydine and Its Derivatives and Their Application to Asymmetric Synthesis

LI Yuhan ^a ,
JIN Rizhe ^b,, ,
GAO Lianxun ^b

a.
a. Branch of Food Engineering, Jilin Business and Technology College, Changchun 130507, China;
b.
b. Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, China

Corresponding author: JIN Rizhe,
Received Date: 8 October 2015
Available Online: 11 December 2015

6-Aryl-6'-bromo-2,2'-bipyridine derivatives 2b~2d were synthesized efficiently from aryl-ethanone by the Krhnke method in one-pot. Then, four chiral 6-[3-((R)-2,2'-diethoxyl-1,1'-binaphthyl)]-2,2'-bipyridine ligands (R)-3a~3d were synthesized by Suzuki coupling of (R)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-2,2' -diethoxyl-1,1'-binaphthyl (R)-1 with 6-bromo-2,2'-bipyridine derivatives 2a~2d. These ligands were applied to asymmetric transfer hydrogenation of acetophenone. The ligand (R)-3a affords 92% of conversion and 4% enantiomeric excess(ee).
- bipyridine,
- chiral,
- binaphthol
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