Hydrolytic kinetic resolution of epoxides: A compromise leads to a nearly perfect catalytic process

ORGN 300

Eric N. Jacobsen, Department of Chemistry and Chemical Biology, Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138
Despite the efforts of many groups over the past decades, no useful methods yet exist for asymmetric epoxidation of terminal olefins. As a result, we have explored alternative strategies for the preparation of enantioenriched terminal epoxides, and this led to the discovery the hydrolytic kinetic resolution (HKR) catalyzed by cobalt salen complexes. This lecture will outline the scope, utility, and mechanism of the HKR process, with emphasis on recent applications of mechanistic insights to the design of novel, highly efficient, and practical multimeric catalysts.