Organic Chemistry

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



We introduce a new reagent class, 2-azatrienes, as a platform for catalytic enantioselective synthesis of allylic amines. Herein, we demonstrate their promise by diasteredivergent and enantioselective synthesis of <i>syn</i>- and <i>anti</i>-1,2-diamines by Cu-bis(phosphine)-catalyzed reductive couplings with imines. With Ph-BPE, <i>anti</i>-diamines are obtained, and with the rarely utilized t-Bu-BDPP, <i>syn</i>-diamines are generated.<br />

Version notes

New data has been added, including more examples of the reductive couplings and a number of mechanistic experiments. The stereochemical model has been revised for the anti-diamine formation.


Thumbnail image of V2 ChemRxiv Preprint Manuscript azatriene-imine coupling.pdf