Ru-catalyzed stereoselective addition of imides to alkynes.
A catalyst system formed in situ from bis(2-methylallyl)cycloocta-1,5-dieneruthenium(II) ((cod)Ru[met]2), a phosphine, and scandium(III) trifluoromethanesulfonate (Sc(OTf)3) was found to efficiently catalyze the anti-Markovnikov addition of imides to terminal alkynes, allowing mild and atom-economic synthesis of enimides. Depending on the phosphine employed, both the (E)- and the (Z)-isomer can be accessed stereoselectively.
Goossen
Lukas J
LJ
Institut für Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Strasse, Building 54, D-67663 Kaiserslautern, Germany. goossen@chemie.uni-kl.de
Blanchot
Mathieu
M
Brinkmann
Claus
C
Goossen
Käthe
K
Karch
Ralph
R
Rivas-Nass
Andreas
A
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D007094:Imides / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*
D000480:Alkynes; D007094:Imides; D012428:Ruthenium