Osmium tetroxide-promoted catalytic oxidative cleavage of olefins: an organometallic ozonolysis.
A mild, organometallic alternative to ozonolysis utilizing oxone and OsO(4) 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.
Travis
Benjamin R
BR
Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
Narayan
Radha S
RS
Borhan
Babak
B