Michael reactions carried out using a bench-top flow system.
The Michael reaction between methyl 1-oxoindan-2-carboxylate and methyl vinyl ketone was achieved successfully by pumping solutions of the reactants in toluene through a fluid bed of Amberlyst A21 at 50 degrees C. The use of a fluid bed reactor is attractive as it allows gel-type beads, i.e. the type of bead used in most studies of polymer-supported (PS) organic reactions, to be used satisfactorily in a flow system. When polymer-supported cinchonidine was used in place of Amberlyst A21, the Michael product was obtained in high yield with an enantiomeric excess (ee) of 51%. This % ee is comparable to that achieved when the reaction was catalysed by cinchonidine itself.
Bonfils
Frederic
F
Department of Chemistry, University of Manchester, Oxford Road, Manchester, UKM13 9PL.
Cazaux
Isabelle
I
Hodge
Philip
P
Caze
Claude
C
D002074:Butanones / Q000737:chemistry; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure
D002074:Butanones; D002930:Cinchona Alkaloids; C057920:3-buten-2-one