A Diastereodivergent and Enantioselective Approach to syn- and anti-Diamines: Development of 2-Azatrienes for Cu-Catalyzed Reductive Couplings with Imines That Furnish Allylic Amines

• DOI: 10.1021/jacs.1c07707
• Publication Date: 2021-08-23T16:23:26Z
• Authors: Pengfei Zhou; Xinxin Shao; Steven J. Malcolmson
• Keywords: Aza Compounds; Heterocyclic Compounds; Molecular Conformation; Stereoisomerism; Imines; Diamines; Oxidation-Reduction; 01 natural sciences; Catalysis; Copper; 0104 chemical sciences

We introduce a new reagent class, 2-azatrienes, as platform for catalytic enantioselective synthesis of allylic amines. Herein, we demonstrate their promise by diastereodivergent syn- and anti-1,2-diamines through Cu-bis(phosphine)-catalyzed reductive couplings with imines. With Ph-BPE the supporting ligand, anti-diamines are obtained (up to 91% yield, >20:1 dr, >99:1 er), rarely utilized t-Bu-BDPP, syn-diamines generated 76% 1:>20 97:3 er).