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

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 d...

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Bibliographic Details
Main Authors: Sílvia D. Fernandes, Riccardo Porta, Pedro C. Barrulas, Alessandra Puglisi, Anthony J. Burke, Maurizio Benaglia
Format: Article
Language:English
Published: MDPI AG 2016-09-01
Series:Molecules
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Online Access:http://www.mdpi.com/1420-3049/21/9/1182
Description
Summary: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.
ISSN:1420-3049