Direct and carbonylative vinylation of steroidal triflates in the presence of homogeneous palladium catalysts.
The palladium-catalyzed vinylation of several steriod 2-enyl- and 3,5-dienyl-3 triflates and estrone-3-triflate was systematically examined using vinyltributylstannane as a vinylating agent. In carbon monoxide atmosphere the insertion of a CO molecule took place and unsaturated ketones were obtained. In this way new steroid derivatives containing unsaturated side chain were produced, which can serve as starting material for further functionalization of the steroid skeleton.
Skoda-Földes
R
R
University of Veszprém, Department of Organic Chemistry, Hungary.
Kollár
L
L
Marinelli
F
F
Arcadi
A
A
D000736:Androstenes / Q000737:chemistry*; D002774:Cholestadienes / Q000737:chemistry*; D004970:Estrone / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis*
D000736:Androstenes; D002774:Cholestadienes; D008698:Mesylates; D014753:Vinyl Compounds; D004970:Estrone; D010165:Palladium; C012077:trifluoromethanesulfonic acid