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

doi:10.11944/j.issn.1000-0518.2016.07.150353

Chinese Journal of Applied Chemistry ›› 2016, Vol. 33 ›› Issue (7): 792-797.DOI: 10.11944/j.issn.1000-0518.2016.07.150353

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

LI Yuhan^a,JIN Rizhe^b^*(),GAO Lianxun^a

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

Received:2015-10-08 Accepted:2015-12-11 Published:2016-06-30 Online:2016-06-30
Contact: JIN Rizhe

Abstract

Abstract:

6-Aryl-6'-bromo-2,2'-bipyridine derivatives 2b~2d were synthesized efficiently from aryl-ethanone by the Kröhnke 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).

Key words: bipyridine, chiral, binaphthol

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.

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

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