Enol esters: versatile substrates for Mannich-type multicomponent reactions.
The interaction of cyclic enol esters with diversely substituted anilines and ethyl glyoxalate yields, under Sc(OTf)3 catalysis, disubstituted N-aryl lactams in a multicomponent reaction. The protocol allows access to the trans stereoisomers after an epimerization of the initial mixture in which the cis isomers predominate. Vinyl acetate yields quinoline derivatives, whereas isopropenyl acetate leads to the corresponding Mannich adducts.
Isambert
Nicolas
N
Institute for Research in Biomedicine, Barcelona Science Park, Josep Samitier 1-5, 08028 Barcelona, Spain.
Cruz
Montse
M
Arévalo
María José
MJ
Gómez
Elena
E
Lavilla
Rodolfo
R
D002384:Catalysis; D004952:Esters; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis; D013237:Stereoisomerism
D004952:Esters; D007769:Lactams; D011804:Quinolines