Metal-free stereoselective additions of activated nucleophiles to β-nitrostyrenes were investigated under continuous-flow conditions in microreactors, in the presence of a chiral bifunctional catalyst. Optimization of the experimental setup gave excellent enantioselectivities (up to 85% e.e.) and higher productivities if compared to the flask syntheses. The potential of this flow chemistry approach was demonstrated by the successful synthesis of an advanced intermediate for the preparation of the GABAB receptor agonist Baclofen.
Continuous-flow stereoselective synthesis in microreactors : nucleophilic additions to nitrostyrenes organocatalyzed by a chiral bifunctional catalyst / S. Rossi, M. Benaglia, A. Puglisi, C. De Filippo, M. Maggini. - In: JOURNAL OF FLOW CHEMISTRY. - ISSN 2062-249X. - 5:1(2015), pp. 17-21.
|Titolo:||Continuous-flow stereoselective synthesis in microreactors : nucleophilic additions to nitrostyrenes organocatalyzed by a chiral bifunctional catalyst|
ROSSI, SERGIO (Corresponding)
BENAGLIA, MAURIZIO (Secondo)
|Parole Chiave:||bifunctional catalyst; flow chemistry; microreactors; nitrostyrenes; organocatalysis; Chemistry (miscellaneous); Fluid Flow and Transfer Processes; Organic Chemistry|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2015|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1556/JFC-D-14-00030|
|Appare nelle tipologie:||01 - Articolo su periodico|