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■ Synthesis of Optically Active γ-Valerolactone and γ-Nonanolactone via Optical Resolution Using Chiral Amine Derived from Amino Acid

Kenichi Yumoto, Morifumi Hasegawa, and Hiroaki Toshima*

*Department of Bioresource Science, College of Agriculture, Ibaraki University, ,

Abstract

Optically active γ-valerolactone and γ-nonanolactone have been synthesized via optical resolution using a newly developed chiral amine derived from L-phenylalanine. Both racemic γ-lactones were transformed to corresponding diastereomeric amides by amidation with the optical resolution agent. Fractional crystallization of diastereomeric amides, recrystallization of each diastereomer, and subsequent hydrolysis gave optically active γ-valerolactone and γ-nonanolactone with sufficient enantiomeric excess and isolated yield. The optical resolution agent was recovered after hydrolysis.