Reductive alkylation of imines via asymmetric Cu-catalyzed addition of organozirconium reagents

Chiral amines are important as medicines or agrochemicals. They are often assembled by nucleophilic addition to corresponding compounds featuring C=N bond. Pre-made organometallics are typical nucleophiles in this reaction. In this work, we describe asymmetric reductive alkylation of imines with alkenes. Hydrozirconation of these alkenes generated organozirconium species in situ. The transformation is catalyzed by Cu-Segphos complex and affords chiral amines in enantioselectivities up to 93% ee. (C) 2020 Elsevier B.V. All rights reserved.