ASYMMETRIC CATALYSIS WITH WATER - EFFICIENT KINETIC RESOLUTION OF TERMINAL EPOXIDES BY MEANS OF CATALYTIC HYDROLYSIS

Epoxides are versatile building blocks for organic synthesis. However, terminal epoxides are arguably the most important subclass of these c ompounds, and no general and practical method exists for their product ion in enantiomerically pure form. Terminal epoxides are available ver y inexpensively as racemic mixtures, and kinetic resolution is an attr active strategy for the production of optically active epoxides, given an economical and operationally simple method. Readily accessible syn thetic catalysts (chiral cobalt-based salen complexes) have been used for the efficient asymmetric hydrolysis of terminal epoxides. This pro cess uses water as the only reagent, no added solvent, and low loading s of a recyclable catalyst (<0.5 mole percent), and it affords highly valuable terminal epoxides and 1,2-diols in high yield with high enant iomeric enrichment.