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Synthesis 2009(9): 1531-1544  
DOI: 10.1055/s-0028-1088045
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Transfer Hydrogenation of Ketimines with Trichlorosilane: Structural Studies

Zhiguo Zhang, Parham Rooshenas, Heike Hausmann, Peter R. Schreiner*
Institut für Organische Chemie, Justus-Liebig-Universität Giessen, Heinrich-Buff-Ring 58, 35392 Giessen, Germany
Fax: +49(641)9934309; e-Mail: prs@org.chemie.uni-giessen.de;
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Publication History

Received 7 February 2009
Publication Date:
14 April 2009 (online)

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Abstract

We report structural and mechanistic studies on the organocatalytic asymmetric transfer hydrogenation of ketimines with trichlorosilane. Amines were obtained in good yields and moderate enantioselectivities. Both experiment and computation were utilized to provide an improved understanding of the mechanism.

Key words

amines - Lewis bases - organocatalysis - transfer hydrogenation - trichlorosilane

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The geometries for structures C1˙C5a and C1˙C5b are given in the supporting information.