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-δ-valerolactone (8, 92% e.e.), (-)-mevalonolactone (9, 58% e.e.), (+)-3-isopropyl-(5-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-dvalerolactone (12) was yielded in a 74% e.e., whose absolute configuration was established to be 2R, 4R.

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