Desymmetrization of Hydrazinocyclohexadienes: A New Approach for the Synthesis of Polyhydroxylated Aminocyclohexanes

Hydrazinocyclohexadienes, easily prepared by an ene-reaction between commercially available azodicarboxylate reagents and cyclohexadiene, are interesting substrates for desymmetrization reactions. Under Sharpless asymmetric dihydroxylation conditions, they can lead efficiently to several chiral building blocks as well as advanced precursors of biologically active compounds.