Malcolmson Lab Develops a New Reagent for Diastereodivergent and Enantioselective Synthesis of Allylic Amines

Malcolmson Lab JACS 2021

Dr. Pengfei Zhou of the Malcolmson Lab, in collaboration with former Malcolmson Lab postdoc Dr. Xinxin Shao, now an assistant professor at Hangzhou Normal University, have developed a new reagent class, 2-azatrienes, that enables the diastereodivergent and enantioselective synthesis of allylic 1,2-diamines through copper-catalyzed reductive couplings with imines. Both syn- and anti-diamines are key fragments in a number of potent bioactive molecules and are each formed selectively in their respective CuH-promoted reactions by the action of two different phosphine ligands. A series of mechanistic studies reveal key aspects of allyl–copper dynamic behavior in the system plus a change in stereodetermining step that occurs with each catalyst and which depends on imine electronics. Read more about this work in The Journal of the American Chemical Society.