Enantioselective Hydrosilylation of Ketones Catalyzed by a Readily Accessible N‐Heterocyclic Carbene–Ir Complex at Room Temperature

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<jats:title>Abstract</jats:title><jats:p>A series of functionalized azolium compounds were synthesized from chiral α‐amino acid derivatives such as β‐amino alcohols. Reaction of hydroxy‐amide‐functionalized azolium salts thus obtained with Ag<jats:sub>2</jats:sub>O afforded N‐heterocyclic carbene‐Ag (NHC–Ag) complexes. Subsequent treatment of the resulting silver compound with [IrCl(cod)]<jats:sub>2</jats:sub> yielded monodentate IrCl(cod)(NHC), which was stable in air. The NHC–Ir complex facilitated efficient asymmetric hydrosilylation of ketones using (EtO)<jats:sub>2</jats:sub>MeSiH under ambient conditions. A chiral ligand containing an isobutyl stereodirecting group was found to be the best ligand for the functionalized NHC–Ir complexes that were examined. A linear relationship was found between the catalyst <jats:italic>ee</jats:italic> and the product <jats:italic>ee</jats:italic>. The hydroxy functional group on the NHC ligand side‐arm not only induced stereocontrol but also enhanced the reaction rate.</jats:p>

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