Reduction and Oxidation of Carbonyl Compounds and Derivatives

Abstract

Reductions and oxidations of carbonyl compounds under a variety of experimental conditions are introduced. We discuss the use of boron and aluminum hydrides, by examining chemo-, regio-, diastereo- and enantioselective processes and point to the advantages that may occur when applying flow chemistry. The regiochemistry in the reduction of α,β-unsaturated carbonyl compounds may provide allylic alcohols (1,2-reduction), saturated carbonyl compounds (1,4-reduction), or products from exhaustive reduction (1,2- and 1,4-reduction). Dissolving metal reductions, heterogeneous and homogeneous hydrogenations using rhodium, ruthenium, and iridium catalysts, reduction via hydrogen transfer reactions, and the hydrosilylation reactions are also discussed. The stereochemical aspects and the enantioselective reductions of carbonyl compounds are addressed, including protocols for their catalytic asymmetric reductions. Examples of enzymatic reductions of ketones, including some large-scale processes that make use of the directed enzymatic evolution strategy, are presented. The oxidation of aldehydes, ketones, and the Baeyer–Villiger, Favorskii, Wolff, Beckmann, and Schmidt rearrangements are presented. Examples of enzymatic Baeyer–Villiger oxidation are also discussed.