Study of the regio- and enantioselectivity of the reactions of osmium tetroxide with allylic alcohols and allylic sulfonamides

Article abstract of DOI:10.1016/S0040-4039(00)77153-X

The regioselectivities of the osmylation of geraniol, its derivatives and geranyl sulfonamides suggest the presence of a moderate attractive interaction between OsO₄ and the allylic groups bearing acidic protons. This allylic directing effect may be due to the development of a hydrogen bonding interaction between OsO₄ and the substrate during the osmylation process. The potential for a hydrogen bond can also have a substantial effect on the enantioselectivities of the osmium tetroxide catalyzed asymmetric dihydroxylation of allylic alcohols.