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

Published

Journal Article

© Georg Thieme Verlag Stuttgart · New York-Synthesis. 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. 1 Introduction 2 Background: Umpolung Strategies for Preparing Chiral Amines 3 Background: 2-Azadienes 4 Reductive Couplings of 2-Azadienes 5 Fluoroarylations of gem -Difluoro-2-azadienes 6 Summary and Outlook.

Full Text

Duke Authors

Cited Authors

  • Malcolmson, SJ; Li, K; Shao, X

Published Date

  • January 1, 2019

Published In

Volume / Issue

  • 30 / 11

Start / End Page

  • 1253 - 1268

Electronic International Standard Serial Number (EISSN)

  • 1437-2096

International Standard Serial Number (ISSN)

  • 0936-5214

Digital Object Identifier (DOI)

  • 10.1055/s-0037-1611770

Citation Source

  • Scopus