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).

Stereoselective reduction of imines with trichlorosilane using solid-supported chiral picolinamides

R. Porta;A. Puglisi;M. Benaglia
2016-09

Abstract

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.
catalytic reactors; chiral picolinamides; flow chemistry; organocatalysis; supported catalysis; trichlorosilane; medicine (all); Organic Chemistry
Settore CHIM/06 - Chimica Organica
MOLECULES
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/454880
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