Asymmetric C-H Oxygenation Reactions

Abstract

This article surveys the catalytic approaches to asymmetric oxygenation of aliphatic C-H groups of organic molecules. The progress of catalysts, both transition metal-based and organocatalysts (excluding enzymatic systems), over the last three decades is analyzed, with a focus on synthetic aspects of the title oxidative transformations. Herewith, stereoselective processes relying on enantioselective oxofunctionalizations (essentially, net hydroxylations) of prochiral C-H groups, as well as oxidative desymmetrizations (through either ketonization or hydroxylation) are considered. This account mostly puts forward environmentally benign processes and catalysts, including biomimetic, or bioinspired, catalyst systems. Basic elements of the state-of-the-art mechanistic landscape of stereoselective C-H oxygenations are discussed briefly.