A Self-Assembled Molecular Cage for Substrate-Selective Epoxidation Reactions in Aqueous Media

Encapsulation of
a manganese porphyrin in a self-assembled molecular
cage allows catalytic epoxidation of various substrates in 1:1 water/acetonitrile
mixtures. The cage acts as a phase-transfer catalyst and creates a
protective environment for the catalyst improving the stability. The
encapsulated catalyst also allows discrimination between styrene derivatives
of various sizes. In a direct competition experiment, the selectivity
of the epoxidation reaction could be inverted with respect to a benchmark
catalyst.