2-Amino ketones from osmium-catalysed oxidations of alkenes

The present article summarises imidoosmium-catalysed oxidations of alkenes to yield 2-amino ketones. Three different approaches are discussed. The first section describes the direct conversion of alkenes to yield racemic 2-amino ketone products in what represents a so-far unknown reactivity in osmium catalysis. It is followed by the description of a two-step procedure, which converts alkenes into enantiomerically pure vicinal amino alcohols followed by stereoselective oxidative conversion into 2-amino ketones. Both pathways derive from a common mechanistic background and constitute a novel side-reaction of the original aminohydroxylation chemistry. An alternative synthetic approach of osmium-catalysed aminohydroxylation of silyl enol ethers is discussed as well and is compared to the previous two procedures.

Graphical abstractThe first examples of direct conversion of alkenes to yield racemic 2-amino ketone products in what represents a so-far unknown reactivity in osmium catalysis are presented. In addition, a two-step procedure, which converts alkenes into enantiomerically pure vicinal amino alcohols followed by stereoselective oxidative conversion into 2-amino ketones is described. Both pathways derive from a common mechanistic background and constitute a novel side-reaction of the original aminohydroxylation chemistry. Figure optionsDownload full-size imageDownload as PowerPoint slide