The effect of A (1, 3)-cis strain on the diastereoselectivity of epoxidation of (E)-and (Z)-6, 6- diethoxy-3-hexen-2-ols and 4-methyl-6, 6-diethoxy-3-hexen-2-ols is analyzed, with some empiric observations provided. Increased A (1, 3)-cis strain results in increased amounts of racemic threo-epoxy alcohols, while high ee's are found for the erythro-epoxy alcohols.