Organocatalytic dimerization of ketoketenes.
A general method for the catalytic dimerization of ketoketenes is described. Tri-n-butylphosphine was found to be the optimal organocatalyst for the racemic reaction. When lithium iodide was used as an additive, the reaction was rendered selective for dimer formation (dimer/trimer > or = 16:1). Ring-opening reactions of the ketoketene dimers as well as preliminary studies toward the development of an asymmetric variant are also reported.
Ibrahim
Ahmad A
AA
Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, USA.
Harzmann
Gero D
GD
Kerrigan
Nessan J
NJ
D002384:Catalysis; D019281:Dimerization; D005030:Ethylenes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D005030:Ethylenes; D007659:Ketones; C008223:ketene