Silica-supported chiral imidazolidinones as organocatalysts in stereoselective reactions under flow conditions
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Data di Pubblicazione:
2013
Citazione:
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.
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.
Tipologia IRIS:
14 - Intervento a convegno non pubblicato
Elenco autori:
V. Chiroli, M. Benaglia, A. Puglisi, R. Porta
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