On the stereoselectivity in bisdihydroxylation of 1,5-cyclooctadiene with osmium tetroxide

Article abstract of DOI:10.1081/SCC-100104460

In the bisdihydroxylation of 1,5-cyclooctadiene with OsO₄, use of a stoichiometric amount of OsO₄ yielded a 1:1 mixture of syn- and anti-isomers, while use of a catalytic amount of OsO₄ gave only syn-(1R*,2S*,5R*,6S*)-cyclooctane-1,2,5,6-tetrol. This syn-selectivity was attributed to the favorable formation of an intramolecular osmium(VI) bisglycolate ester in the catalytic reaction.