Shiliu Chen, Shaozhong Wang
An iridium-catalyzed enantioselective N-allylation of aminoquinones with racemic allylic alcohols has been developed, affording chiral aminoquinone derivatives in excellent yields (up to 96%) and with high enantioselectivities (up to 99% ee). The reaction exhibits a broad substrate scope, encompassing aryl-, alkyl-, and heterocyclic-substituted allylic alcohols as well as a diverse range of aminoquinones. The observed chemoselectivity in this asymmetric allylation is proposed to arise from tautomerization of the aminoquinone, which makes nitrogen rather than carbon the nucleophilic site.