Ruthenium-Catalyzed Stereoselective anti-Markovnikov-Addition of Thioamides to Alkynes

被引：39

作者：

Goossen, Lukas J. ^{[1
]}

Blanchot, Mathieu ^{[1
]}

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

Karch, Ralf ^{[2
]}

Rivas-Nass, Andreas ^{[2
]}

机构：

[1] TU Kaiserslautern, Fachbereich Chem, D-67663 Kaiserslautern, Germany

[2] UMICORE AG & CO KG, D-63457 Hanau, Germany

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 20期

关键词：

D O I：

10.1021/ol801736h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalyst system generated in situ from bis(2-methallyl)-cycloocta-1,5-diene-ruthenium(II) and a phosphine was found to efficiently catalyze the addition of thioamides to terminal alkynes with exclusive formation of the anti-Markovnikov thioenamide products. The stereoselectivity of the addition is usually high and controlled by the choice of the phosphine ligand, whereas the (E)-isomers are predominantly formed in the presence of tri(n-octyl)phosphine, the use of bis(dicyclohexylphosphino)methane preferentially leads to the formation of the (Z)-configured thioenamides.

引用

页码：4497 / 4499

页数：3

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