Synthesis and asymmetric hydrogenation of 3,5-dioxoheptanedioates. Preparation of enantiomerically pure substituted δ-valerolactones

The synthesis of 3,5-dioxoheptanedioic acid derivatives based on the reaction of ketene with malonyl chloride was developed. Resulting diketones were subjected to Ru–(S)-BINAP-catalyzed asymmetric hydrogenation. The products were transformed into enantiomerically pure 3,5-substituted-δ-valerolactones.