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

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.

SUBMITTER: Fernandes SD

PROVIDER: S-EPMC6274114 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature

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

Fernandes Sílvia D SD Porta Riccardo R Barrulas Pedro C PC Puglisi Alessandra A Burke Anthony J AJ Benaglia Maurizio M

Molecules (Basel, Switzerland) 20160906 9

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 d ...[more]

PMID: 27608000

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