"The inherent strain (-27 kcal/mol) of epoxides makes them prone to (1) ring opening by a wide range of nucleophiles, (2) base-induced rearrangement, and (3) acid-catalyzed isomerization. … Generally, nucleophilic opening of an unsymmetrically substituted epoxide is regioselective. … . In cyclohexane derivatives, opening of the epoxide ring with nucleophilic reagents proceeds stereospecifically in the majority of cases via an S,2 reaction, placing the oxygen of the epoxide and the attacking nucleophile in a trans- and diaxial-relationship. Thus, a single diastereomer of an epoxide gives upon ring opening a single diastereomer of the product."