An Asymmetric Synthesis of 2,4-Dimethylvalerolactone and Mevalonolactone using Chiral Binaphthyldiamine Derivatives

Article abstract of DOI:10.1039/c39840000779

Axially dissymmetric binaphthyldiamine derivatives formed by asymmetric ring opening of the cyclic anhydrides (3) and (4) ring close on hydrolysis to give (-)-cis-2,4-dimethylvalerolactone (6) and (-)-mevalonolactone (7) in 92percent and 58percent enantiomeric excess (e.e.), respectively; similarly the derivative of the racemic cyclic anhydride (+/-)-(3) ring closes to give (-)-trans-2,4-dimethylvalerolactone with 74percent e.e.