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  • Title: Ruthenium-catalyzed stereoselective anti-Markovnikov-addition of thioamides to alkynes.
    Author: Goossen LJ, Blanchot M, Salih KS, Karch R, Rivas-Nass A.
    Journal: Org Lett; 2008 Oct 16; 10(20):4497-9. PubMed ID: 18800846.
    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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