Open AccessA Diastereodivergent and Enantioselective Approach to syn- and anti-Diamines: Development of 2-Azatrienes for Cu-Catalyzed Reductive Couplings with Imines That Furnish Allylic Amines
Author(s) -
Pengfei Zhou,
Xinxin Shao,
Steven J. Malcolmson
Publication year - 2021
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.1c07707
Subject(s) - chemistry , allylic rearrangement , enantioselective synthesis , yield (engineering) , phosphine , catalysis , reagent , ligand (biochemistry) , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , receptor , biochemistry , materials science , metallurgy
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).