A number of epoxide hydrolase (EH)-mediated bioconversions have been developed to prepare single enantiomeric product from racemic substrates with a yield greater than 50%. Enantioconvergent hydrolysis using single or two EHs possessing complementary enantio- and regio-selectivity, EH-based chemoenzymatic reactions, and EH-triggered cascade-reactions have been developed for the preparation of chiral epoxides, epoxyalcohols, tetrahydrofuran derivatives and vicinal diols. All these bioconversions are based on stereochemical flexibilities of various EHs and can be used in total synthesis of biologically active compounds without the formation of unwanted enantiomers.