The chemistry of epoxy alcohols

Epoxy alcohols are extremely versatile building blocks in organic synthesis, due to their general availability in both enantiomeric series. The preferred methods for the subsequent stereoselective attack of various nucleophiles (hydride, carbon nucleophiles, nitrogen nucleophiles, oxygen nucleophiles, halogen ions, etc.) in a regioselective fashion at C-2 and C-3 are reviewed. The application of some of these methods in the synthesis of natural products and optically active compounds are described. Finally some reactions typical of homoallylic alcohols and their corresponding hydroxyepoxides are also reported.