The so called MacMillan imidazolidinone organocatalysts are suitable for many stereoselective reactions undergoing through the formation of the iminium ion as activated species. Given its popularity, it is not surprising that it has been covalently immobilized both on soluble and insoluble supports. The use of the (S)-tyrosine-derived imidazolidinone anchored on silica as organocatalyst under flow chemistry conditions is described for the first time in this work. An HPLC column filled with the silica-supported catalyst was tested in the enantioselective Diels-Alder cycloaddition of cinnamaldehyde with cyclopentadiene. In comparison with batch conditions the process showed to be time saving maintaining both a good chemical activity and enantioselectivity for a long period of time, facilitating the isolation of the final product and avoiding the recovery step of the catalyst.

Silica-supported chiral imidazolidinones as organocatalysts in stereoselective reactions under flow conditions / V. Chiroli, M. Benaglia, A. Puglisi, R. Porta. ((Intervento presentato al 3. convegno International Conference of the Flow Chemistry Society tenutosi a München nel 2013.

Silica-supported chiral imidazolidinones as organocatalysts in stereoselective reactions under flow conditions

V. Chiroli;M. Benaglia;A. Puglisi;R. Porta
2013-03

Abstract

The so called MacMillan imidazolidinone organocatalysts are suitable for many stereoselective reactions undergoing through the formation of the iminium ion as activated species. Given its popularity, it is not surprising that it has been covalently immobilized both on soluble and insoluble supports. The use of the (S)-tyrosine-derived imidazolidinone anchored on silica as organocatalyst under flow chemistry conditions is described for the first time in this work. An HPLC column filled with the silica-supported catalyst was tested in the enantioselective Diels-Alder cycloaddition of cinnamaldehyde with cyclopentadiene. In comparison with batch conditions the process showed to be time saving maintaining both a good chemical activity and enantioselectivity for a long period of time, facilitating the isolation of the final product and avoiding the recovery step of the catalyst.
Settore CHIM/06 - Chimica Organica
Silica-supported chiral imidazolidinones as organocatalysts in stereoselective reactions under flow conditions / V. Chiroli, M. Benaglia, A. Puglisi, R. Porta. ((Intervento presentato al 3. convegno International Conference of the Flow Chemistry Society tenutosi a München nel 2013.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/238807
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