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Molecules 2016, 21(9), 1182; doi:10.3390/molecules21091182

Stereoselective Reduction of Imines with Trichlorosilane Using Solid-Supported Chiral Picolinamides

1
Department of Chemistry and Chemistry Center of Évora, School of Science and Technology and Institute for Research and Advanced Studies, University of Évora, Rua Romão Ramalho 59, Évora 7000, Portugal
2
Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, Milano 20133, Italy
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 28 July 2016 / Revised: 30 August 2016 / Accepted: 1 September 2016 / Published: 6 September 2016
(This article belongs to the Special Issue Recent Advancements in Polymer-Supported Catalysis)
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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. View Full-Text
Keywords: supported catalysis; catalytic reactors; trichlorosilane; chiral picolinamides; organocatalysis; flow chemistry supported catalysis; catalytic reactors; trichlorosilane; chiral picolinamides; organocatalysis; flow chemistry
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Fernandes, S.D.; Porta, R.; Barrulas, P.C.; Puglisi, A.; Burke, A.J.; Benaglia, M. Stereoselective Reduction of Imines with Trichlorosilane Using Solid-Supported Chiral Picolinamides. Molecules 2016, 21, 1182.

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