2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.

Journal Article (Journal Article)

The development of new strategies for the preparation of chiral amines is an important objective in organic synthesis. In this Synpacts , we summarize our approach for catalytically accessing nucleophilic aminoalkyl metal species from 2-azadienes, and its application in generating a number of important but elusive chiral amine scaffolds. Reductive couplings with ketones and imines afford 1,2-amino tertiary alcohols and 1,2-diamines, respectively, whereas fluoroarylations of gem -difluoro-2-azadienes deliver α-trifluoromethylated benzylic amines.

Full Text

Duke Authors

Cited Authors

  • Malcolmson, SJ; Li, K; Shao, X

Published Date

  • July 2019

Published In

Volume / Issue

  • 30 / 11

Start / End Page

  • 1253 - 1268

PubMed ID

  • 33731976

Pubmed Central ID

  • PMC7963344

International Standard Serial Number (ISSN)

  • 0936-5214

Digital Object Identifier (DOI)

  • 10.1055/s-0037-1611770


  • eng