Dynamic Kinetic Asymmetric Amination of Alcohols: From A Mixture of Four Isomers to Diastereo- and Enantiopure α‑Branched Amines

The
first dynamic kinetic asymmetric amination of alcohols via
borrowing hydrogen methodology is presented. Under the cooperative
catalysis by an iridium complex and a chiral phosphoric acid, α-branched
alcohols that exist as a mixture of four isomers undergo racemization
by two orthogonal mechanisms and are converted to diastereo- and enantiopure
amines bearing adjacent stereocenters. The preparation of diastereo-
and enantiopure 1,2-amino alcohols is also realized using this catalytic
system.