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 typ...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 4; no. 3; p. 493
Main Authors Bonfils, Frederic, Cazaux, Isabelle, Hodge, Philip, Caze, Claude
Format Journal Article
LanguageEnglish
Published England 07.02.2006
Subjects
Butanones - chemistry
Catalysis
Cinchona Alkaloids - chemistry
Models, Chemical
Molecular Structure
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Summary: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.
ISSN:1477-0520
DOI:10.1039/b515241k