Selective Asymmetric Dihyroxylation of Polyenes

Article abstract of DOI:10.1016/0040-4020(94)01021-Q

The asymmetric dihydroxylation procedure (AD) is applied to a variety of polyenes.In many cases excellent regioselectivities are obtained.The observed selectivities are rationalized in terms of electronic and/or steric inherent to the substrate, superimposed on the substrate's favorable or unfavorable interactions with the binding pocket of the AD ligand.Surprisingly, for medium and large ring olefins with trans-double bonds outstanding enantioselectivities are realized using the pyrimidine ligands.A hexaol of D₃ symmetry is prepared from all trans cyclodecatriene.