A Diastereodivergent and Enantioselective Approach to <i>syn</i> - and <i>anti</i> -Diamines: Development of 2-Azatrienes for Cu-Catalyzed Reductive Couplings with Imines That Furnish Allylic Amines
Pengfei Zhou, Xinxin Shao, Steven J. Malcolmson
Abstract
We introduce a new reagent class, 2-azatrienes, as a platform for catalytic enantioselective synthesis of allylic amines. Herein, we demonstrate their promise by a diastereodivergent synthesis of syn- and anti-1,2-diamines through their Cu–bis(phosphine)-catalyzed reductive couplings with imines. With Ph-BPE as the supporting ligand, anti-diamines are obtained (up to 91% yield, >20:1 dr, and >99:1 er), and with the rarely utilized t-Bu-BDPP, syn-diamines are generated (up to 76% yield, 1:>20 dr, and 97:3 er).
Topics & Concepts
ChemistryEnantioselective synthesisAllylic rearrangementCatalysisOrganic chemistryCombinatorial chemistryStereochemistryMedicinal chemistryAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsChemical Synthesis and Analysis