Synthesis of atropoisomeric pyridines via cobalt-catalyzed cocyclotrimerization of diynes with benzonitrile

被引：31

作者：

Hrdina, R

Stará, IG

Dufková, L

Mitchel, S

Císarová, I

Kotora, M

机构：

[1] Charles Univ Prague, Fac Sci, Dept Organ & Nucl Chem, CR-12843 Prague 2, Czech Republic

[2] Acad Sci Czech Republ, Inst Organ Chem & Biochem, Prague 16610 6, Czech Republic

[3] Charles Univ Prague, Fac Sci, Dept Inorgan Chem, CR-12843 Prague 2, Czech Republic

来源：

TETRAHEDRON | 2006年 / 62卷 / 05期

关键词：

pyridine; cocyclotrimerization; cobalt; catalysis; organocatalysis;

D O I：

10.1016/j.tet.2005.10.034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Arylpyridines (precursors for potential organocatalysts) are easily accesible by cobalt-catalyzed cocyclotrimerization of ortho-substituted 1-aryl-1,7-octadiynes with benzonitrile. The scope of the reaction with respect to the ortho substituents (OMe, Me, COOMe, NHCOMe, F, etc.) was investigated. Three potentially atropoisomeric arylpyridines were prepared and one of them was converted into the corresponding N-oxide and resolved into its enantiomers. The absolute configuration of the N-oxide was established by X-ray crystal structure analysis. Preliminary results of its application in asymmetric organocatalysis are presented. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：968 / 976

页数：9

共 83 条

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