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

26 July 2021, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

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 diasteredivergent and enantioselective synthesis of syn- and anti-1,2-diamines by Cu-bis(phosphine)-catalyzed reductive couplings with imines. With Ph-BPE, anti-diamines are obtained, and with the rarely utilized t-Bu-BDPP, syn-diamines are generated.

Keywords

umpolung
azatrienes
imines
1,2-diamines
diastereodivergent
enantioselective
copper hydride
phosphine

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