Stereoselective Ring-Opening Reactions of Epoxides in Water

Water has proved to be an excellent reaction medium for the definition of highly chemically-efficient and environmentally-friendly synthetic processes. In several cases, by exploiting the unique properties of water it has been possible to realize more selective and efficient processes than those performed in organic media, including the ring-opening of epoxides by nucleophiles. In this review article the role of water in influencing the stereoselectivity of epoxide ring-opening reactions will be presented, including the most recent examples of enzyme-catalyzed processes.