ChemInform Abstract: Chemoselective Reaction on a Hydroxy or Aldehyde Group Tethered with a Tri-Substituted Ozonide: A Versatile Methodology for the Preparation of Terminally Differentiated Compounds from Cyclohexene.

Abstract Molecules containing a hydroxy or aldehyde group tethered with a tri-substituted ozonide moiety were prepared. We have demonstrated that the ozonide group is stable under certain Lewis acidic, free radical, and organometallic conditions. Therefore, chemoselective elaboration of the hydroxy or aldehyde group is possible under these conditions. These functional group transformations followed by the decomposition of the ozonide moiety provided an extremely convenient and versatile way to prepare terminally differentiated compounds from symmetric cyclohexene.