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Asymmetric ring opening of the cyclic acid anhydrides cis-2, 3 ~ 6 with the axially dissymmetric binaphthyldiamines (S)-1a~d and subsequent esterification gave diastereoisomeric mixtures of the amide-esters 7a ~ h. Successive reduction of the ester group and ring closure by hydrolysis afforded ( – )-cis-2,4-dimethyl-δ5-valerolactone (8, 92% e.e.), ( – )-mevalonolactone (9, 58% e.e.), ( + )-3-isopropyl-δ-valerolactone (10, 42% e.e.), and ( + )-2,3-methylene-γ-butyrolactone (11, 46% e.e.). Through kinetic resolution of the racemic anhydride trans-2, ( – )-trans-2,4-dimethyl-δ-valerolactone (12) was yielded in a 74% e.e., whose absolute configuration was established to be 2R,4R.

An asymmetric synthesis of lactones from cyclic acid anhydrides with chiral binaphthyldiamines.