An N-heterocyclic carbene iridium catalyst with metal-centered chirality for enantioselective transfer hydrogenation of imines.

Abstract

A cyclometalating N-heterocyclic carbene iridium complex featuring metal-centered chirality was designed and used for the asymmetric transfer hydrogenation (ATH) of imines. Four strongly σ-donating carbon-based substituents (2 carbenes and 2 phenyl moieties), a chirality transfer directly from the stereogenic metal center to the C[double bond, length as m-dash]N bond of substrates, as well as a restriction of catalyst deactivation by steric demanding substituents, render the new complex one of the most efficient catalysts for ATH of cyclic N-sulfonylimines (down to 0.01 mol% cat., 24 examples, 94-98% ee).