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Catalytic Enantioselective Synthesis of Silicon-Stereogenic Alkoxysilanes and Siloxanes

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A Rh-catalyzed enantioselective intermolecular dehydrogenative Si–O coupling of dihydrosilanes with alcohols and silanols is demonstrated. Rh(I) catalyst equipped with a Josiphos ligand enables the highly enantioselective alcoholysis process of dihydrosilanes,… Click to show full abstract

A Rh-catalyzed enantioselective intermolecular dehydrogenative Si–O coupling of dihydrosilanes with alcohols and silanols is demonstrated. Rh(I) catalyst equipped with a Josiphos ligand enables the highly enantioselective alcoholysis process of dihydrosilanes, giving access to a variety of functionalized triorgano-substituted silicon-stereogenic alkoxysilanes and siloxanes in decent yields and ee, which significantly expand the chemical space of the silicon-centered chiral molecules. Utility of this methodology is illustrated by the construction of circularly polarized luminescence (CPL) active chiral alkoxysilane small organic molecules. 1 Introduction 2 Conditions Optimization 3 Substrate Scope 4 Application 5 Conclusions 6 Experimental Procedure

Keywords: alkoxysilanes siloxanes; silicon stereogenic; silicon; stereogenic alkoxysilanes; catalytic enantioselective; enantioselective synthesis

Journal Title: Synlett
Year Published: 2021

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