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 back.-round and constitute a novel side-reaction of the original ammohydroxylation chemistry. An alternative synthetic approach of osmium-catalysed ammohydroxylation of silyl enol ethers is discussed as well and is compared to the previous two procedures. (c) 2006 Elsevier B.V. All rights reserved.