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Updated: Jul 17, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Conformational rigidity of silicon-stereogenic silanes in asymmetric catalysis: A comparative study
Sebastian Rendler1, Martin Oestreich
1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, D-48149 Münster, Germany. sebastian.rendler@uni-muenster.de
Abstract:
In recent years, cyclic silicon-stereogenic silanes were successfully employed as stereoinducers in transition metal-catalyzed asymmetric transformations as exemplified by (1) the hydrosilylation of alkenes constituting a chirality transfer from silicon to carbon and (2) the kinetic resolution of racemic mixtures of alcohols by dehydrogenative silicon-oxygen coupling. In this investigation, a cyclic and a structurally related acyclic silane with silicon-centered chirality were compared using the above-mentioned model reactions. The stereochemical outcome of these pairs of reactions was correlated with and rationalized by the current mechanistic pictures. An acyclic silicon-stereogenic silane is also capable of inducing excellent chirality transfer (ct) in a palladium-catalyzed intermolecular carbon-silicon bond formation yet silicon incorporated into a cyclic framework is required in the copper-catalyzed silicon-oxygen bond forming reaction.
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