Indium Tribromide Catalyzed Coupling Reaction of Enol Ethers with Silyl Ketene Imines toward the Synthesis of β,γ-Unsaturated Nitriles

被引：21
|
作者：
Nishimoto, Yoshihiro [1 ,2 ]
Nishimura, Takashi [1 ]
Yasuda, Makoto [1 ]
机构：
[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[2] Osaka Univ, Grad Sch Engn, Frontier Res Base Young Researchers, Suita, Osaka 5650871, Japan
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 50期
关键词：
cross-coupling; enol ethers; indium; silicon; silyl ketene imines; PETERSON OLEFINATION REACTION; ENANTIOSELECTIVE CONSTRUCTION; ASYMMETRIC-SYNTHESIS; GALLIUM TRIBROMIDE; MANNICH REACTION; ALPHA-ARYLATION; SIMPLE ALKENES; DERIVATIVES; VERAPAMIL; ACETALS;
D O I：
10.1002/chem.201503414
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Herein, a coupling reaction of enol ethers with silyl ketene imines in the presence of catalytic amounts of InBr3 and Me3SiBr is described. Kinetic studies have revealed that an indium catalyst and Me3SiBr accelerated the coupling process and the regeneration of the catalyst, respectively. Various types of enol ethers and silyl ketene imines are applicable. In addition, a formal synthesis of verapamil was achieved by using this novel coupling reaction.
引用
收藏
页码：18301 / 18308
页数：8
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