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Enantioselective Hydrosilylation of β,β‐Disubstituted Enamides to Construct α‐Aminosilanes with Vicinal Stereocenters

Wenwen Zhang, Bi‐Jie Li

2022Angewandte Chemie International Edition30 citationsDOI

Abstract

Despite the advances in the area of catalytic alkene hydrosilylation, the enantioselective hydrosilylation of alkenes bearing a heteroatom substituent is scarce. Here we report a rhodium-catalyzed hydrosilylation of β,β-disubstituted enamides to directly afford valuable α-aminosilanes in a highly regio-, diastereo-, and enantioselective manner. Stereodivergent synthesis could be achieved by regulating substrate geometry and ligand configuration to generate all the possible stereoisomers in high enantio-purity.

Topics & Concepts

Enantioselective synthesisHydrosilylationStereocenterAlkeneChemistrySubstituentHeteroatomStereochemistryLigand (biochemistry)CatalysisOrganic chemistryRing (chemistry)BiochemistryReceptorAsymmetric Hydrogenation and CatalysisOrganoboron and organosilicon chemistryCatalytic C–H Functionalization Methods
Enantioselective Hydrosilylation of β,β‐Disubstituted Enamides to Construct α‐Aminosilanes with Vicinal Stereocenters | Litcius