Osmium Tetroxide Promoted Catalytic Oxidative Cleavage of Olefins: An Organometallic Ozonolysis.

A mild, organometallic alternative to ozonolysis utilizing oxone and OsO4 is presented. This is a direct oxidation of olefins via the carbon−carbon cleavage of an osmate ester by the action of oxone. Twenty-four different olefins were converted to their corresponding ketones or carboxylic acids in high yields (>80%). Free alcohols, acetate- and benzyl-protected alcohols, and 1,2-diols were stable under these conditions. This method should be applicable for traditional organic synthesis.