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Catalytic Enantioselective Synthesis of Silicon-Stereogenic Alkoxysilanes and Siloxanes

Chuan He, Jiefeng Zhu

2021Synlett16 citationsDOI

Abstract

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

Topics & Concepts

Enantioselective synthesisSilanesStereocenterChemistryAlkoxy groupCatalysisSiliconSubstrate (aquarium)Ligand (biochemistry)Combinatorial chemistryOrganic chemistryMoleculeAlkylSilaneGeologyReceptorOceanographyBiochemistrySynthesis and Properties of Aromatic CompoundsOrganoboron and organosilicon chemistrySynthesis and characterization of novel inorganic/organometallic compounds