Asymmetric Catalysis by a Chiral Ruthenium Porphyrin:  Epoxidation, Hydroxylation, and Partial Kinetic Resolution of Hydrocarbons

A new member of our D2 symmetry ruthenium porphyrins is shown to be a most selective catalyst for asymmetric epoxidation of terminal and trans-disubstituted olefins. The same catalyst displays some selectivity in kinetic resolution of secondary alcohols and in what appears to be the first example of catalytic enantioselective hydroxylation of tertiary alkanes.