A highly regio- and enantioselective copper-catalyzed three-component coupling of isocyanides, hydrosilanes, and γ,γ-disubstituted allylic phosphates/chlorides to afford chiral α-quaternary formimides was enabled by the combined use of our original chiral naphthol-carbene ligand as a functional Cu-supporting ligand and LiOtBu as a stoichiometric Lewis base for Si. The formimides were readily converted to α-quaternary aldehydes.
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Synthesis of α-Quaternary Formimides and Aldehydes through Umpolung Asymmetric Copper Catalysis with Isocyanides.
J Am Chem Soc
February 2017
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan.
A highly regio- and enantioselective copper-catalyzed three-component coupling of isocyanides, hydrosilanes, and γ,γ-disubstituted allylic phosphates/chlorides to afford chiral α-quaternary formimides was enabled by the combined use of our original chiral naphthol-carbene ligand as a functional Cu-supporting ligand and LiOtBu as a stoichiometric Lewis base for Si. The formimides were readily converted to α-quaternary aldehydes.
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