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.

Journal Article (Journal Article)

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).

Full Text

Duke Authors

Cited Authors

  • Zhou, P; Shao, X; Malcolmson, SJ

Published Date

  • September 2021

Published In

Volume / Issue

  • 143 / 34

Start / End Page

  • 13999 - 14008

PubMed ID

  • 34424694

Pubmed Central ID

  • PMC8450874

Electronic International Standard Serial Number (EISSN)

  • 1520-5126

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/jacs.1c07707


  • eng