Umpolung of Enamines: An Overview on Strategies and Synthons

Published as part of the Special Section 11th EuCheMS Organic Division Young Investigator Workshop

Abstract

Umpolung strategies are of considerable interest to organic chemists because they provide alternative synthetic routes to those imposed by the natural polarity of classical synthons. Reverse-polarity reactions of aldehydes, α,β-unsaturated carbonyl compounds, and imines are deeply embedded in the methodology of organic synthesis. In recent years, umpolung of enols and enamines has received much attention as a novel strategy to access α-substituted ketones. Here, state-of-the-art approaches to umpolung of enamine reactivity are discussed, with a particular focus on recent developments in this field from the author’s research group.

1 Introduction

2 Approaches toward Umpolung of Enamines

3 Umpolung of Enamines through Single-Electron Oxidation

4 Azadienes as Synthetic Equivalents of Enamine Umpolung Synthons

5 Enamines Possessing a Leaving Group at the Nitrogen Atom

6 Enamines Possessing a Directing Group at the Nitrogen Atom

7 Summary and Outlook

Key words

umpolung - enamines - ketones - nitro compounds - imines

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