ON THE STEREOSELECTIVITY IN BISDIHYDROXYLATION OF 1,5-CYCLOOCTADIENE WITH OSMIUM TETROXIDE

Abstract

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.

Acknowledgments