Ruthenium-Catalyzed Addition of Primary Amides to Alkynes: A Stereoselective Synthesis of Secondary Enamides

被引：23

作者：

Goossen, Lukas J. ^{[1
]}

Blanchot, Mathieu ^{[1
]}

Salih, Kifah S. M. ^{[1
]}

Goosen, Kaethe ^{[1
]}

机构：

[1] Tech Univ Kaiserslautern, Fachbereich Chem, D-67663 Kaiserslautern, Germany

来源：

SYNTHESIS-STUTTGART | 2009年 / 13期

关键词：

alkynes; amides; enamides; hydroamidation; ruthenium; CARBOXYLIC-ACIDS; HYDROAMINATION; DERIVATIVES; ALDEHYDES; HYDRATION;

D O I：

10.1055/s-0029-1216847

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The anti-Markovnikov addition of primary amides to terminal alkynes under the formation of 7 configured secondary enamides is efficiently promoted by a catalyst system generated in situ from bis(2-methallyl)(cycloocta-1,5-diene)ruthenium(II), 1,4-bis(dicyclohexylphosphino)butane, and ytterbium triflate. The thermodynamically more stable E-isomers are accessible by combining the above hydroamidation with an in situ double-bond isomerization reaction, using triethylamine and molecular sieves.

引用

页码：2283 / 2288

页数：6

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