The stereoselective reduction of imines with trichlorosilane catalyzed by chiral Lewis bases is a well-established procedure for the synthesis of enantio-enriched amines. Five supported cinchona-based picolinamides have been prepared and their activity tested in a model reaction. The comparison of different supporting materials revealed that polystyrene gave better results than silica in terms of stereoselectivity. The applicability of the solid-supported catalyst of choice to the reduction of different imines was also demonstrated. Additionally, for the first time, a catalytic reactor containing a polymer-immobilized chiral picolinamide has been employed for the stereoselective reduction of imines with trichlorosilane under continuous flow conditions.
Stereoselective reduction of imines with trichlorosilane using solid-supported chiral picolinamides / S.D. Fernandes, R. Porta, P.C. Barrulas, A. Puglisi, A.J. Burke, M. Benaglia. - In: MOLECULES. - ISSN 1420-3049. - 21:9(2016 Sep).
|Titolo:||Stereoselective reduction of imines with trichlorosilane using solid-supported chiral picolinamides|
PORTA, RICCARDO (Corresponding)
BENAGLIA, MAURIZIO (Ultimo)
|Parole Chiave:||catalytic reactors; chiral picolinamides; flow chemistry; organocatalysis; supported catalysis; trichlorosilane; medicine (all); Organic Chemistry|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||set-2016|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.3390/molecules21091182|
|Appare nelle tipologie:||01 - Articolo su periodico|