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Note | Regular issue | Vol 81, No. 2, 2010, pp.421-431
Published online, 27th November, 2009
DOI: 10.3987/COM-09-11863
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, ,


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.