Asymmetric Synthesis of Axially Chiral 1-Aryl-5,6,7,8-tetrahydroquinolines by Cobalt-Catalyzed [2+2+2] Cycloaddition Reaction of 1-Aryl-1,7-octadiynes and Nitrites

被引：111

作者：

Hapke, Marko ^{[1
]}

Kral, Karolin ^{[1
]}

Fischer, Christine ^{[1
]}

Spannenberg, Anke ^{[1
]}

Gutnov, Andrey ^{[1
]}

Redkin, Dmitry ^{[1
]}

Heller, Barbara ^{[1
]}

机构：

[1] Univ Rostock, Leibniz Inst Katalyse eV LIKAT, D-18059 Rostock, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 12期

关键词：

ENANTIOMERIZATION RATE CONSTANTS; ARYL BOND FORMATION; ONE-STEP SYNTHESIS; SUZUKI-MIYAURA; ENANTIOSELECTIVE CONSTRUCTION; 2,2'-BIPYRIDINE LIGANDS; COUPLING REACTIONS; NITRILES; PYRIDINES; CYCLOTRIMERIZATION;

D O I：

10.1021/jo100122d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of a range of axially chiral 2-arylpyridines by a cobalt-catalyzed [2 + 2 + 2] cycloaddition reaction is described. The use of a planar chiral (1-neomenthylindenyl)cobalt(COD) complex under photochemical conditions is the key for reacting the 1-naphthyldiynes with a range of differently functionalized nitriles, giving the enantiomeric atropoisomers with high chemical yields and enantiomcric excesses of up to 94% ee.

引用

页码：3993 / 4003

页数：11

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