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

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...

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Published inOrganic letters Vol. 10; no. 20; pp. 4497 - 4499
Main Authors Goossen, Lukas J, Blanchot, Mathieu, Salih, Kifah S. M, Karch, Ralf, Rivas-Nass, Andreas
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.10.2008
Amer Chemical Soc
Subjects
Alkynes - chemical synthesis
Alkynes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Molecular Structure
Physical Sciences
Ruthenium - chemistry
Science & Technology
Stereoisomerism
Sulfhydryl Compounds - chemistry
Thioamides - chemistry
THIOENAMIDE PHOTOCHEMISTRY
ESTERS
IMIDES
HYDRATION
CARBOXYLIC-ACIDS
ENAMIDES
AMIDES
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol801736h