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
