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 in | Organic letters Vol. 10; no. 20; pp. 4497 - 4499 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
American Chemical Society
16.10.2008
Amer Chemical Soc |
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| Abstract | 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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| AbstractList | 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. |
| Author | Blanchot, Mathieu Goossen, Lukas J Karch, Ralf Salih, Kifah S. M Rivas-Nass, Andreas |
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| Cites_doi | 10.1055/s-2007-966002 10.1021/ol702564e 10.1002/anie.200462844 10.1021/cr030035s 10.1039/b200386b 10.1021/jo061966h 10.1055/s-2006-942452 10.1039/b211277a 10.1021/jo00257a038 10.1021/ol0003937 10.1016/0223-5234(88)90194-8 10.1021/ja0119292 10.1016/S0040-4020(01)88445-3 10.1016/S0040-4020(01)91137-8 10.1021/jo00013a027 10.1021/jo00178a032 10.1002/anie.200300616 10.1016/S0022-328X(97)00435-X 10.1021/jo00209a051 |
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| Keywords | THIOENAMIDE PHOTOCHEMISTRY ESTERS IMIDES HYDRATION CARBOXYLIC-ACIDS ENAMIDES AMIDES |
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| Snippet | 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... |
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| SubjectTerms | Alkynes - chemical synthesis Alkynes - chemistry Catalysis Chemistry Chemistry, Organic Molecular Structure Physical Sciences Ruthenium - chemistry Science & Technology Stereoisomerism Sulfhydryl Compounds - chemistry Thioamides - chemistry |
| Title | Ruthenium-Catalyzed Stereoselective anti-Markovnikov-Addition of Thioamides to Alkynes |
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