Recent Studies on the Regioselective C-Protonation of Enol Derivatives using Carbonyl-Containing Proton Donors

Abstract

Enolate protonation can occur by two different pathways. With strong acids regioselective protonation generally occurs on the oxygen of the enolate to give an enol and then acid catalysed tautomerisation leads directly to the thermody-namically preferred carbonyl motif. However, with much weaker acids kinetic protonation on carbon can occur to give directly the carbonyl derivative. This review discuss recent developments into the use of chelating acids to promote this stereochemically important C-protonation and we comment on factors that appear to promote this selectivity.