Preparation of Optically Pure δ-Lactones Using Diastereomeric Resolution with Amino Acid as Resolving Agent

Synthesis of optically pure δ-lactones by diastereomeric resolution was investigated. Amino acid derivatives, which can be obtained at a relatively low cost, were used as resolving agents. Six optically pure δ-lactones were efficiently synthesized using Cbz-L-alanine without other expensive resolvin...

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Veröffentlicht in:Journal of Oleo Science 2015, Vol.64(1), pp.75-90
Hauptverfasser: Shimotori, Yasutaka, Hoshi, Masayuki, Seki, Syota, Osanai, Takeshi, Okabe, Hayato, Ikeda, Yoshitaka, Miyakoshi, Tetsuo
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Sprache:eng
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Zusammenfassung:Synthesis of optically pure δ-lactones by diastereomeric resolution was investigated. Amino acid derivatives, which can be obtained at a relatively low cost, were used as resolving agents. Six optically pure δ-lactones were efficiently synthesized using Cbz-L-alanine without other expensive resolving agents. Both enantiomers of δ-lactone obtained had over 98% enantiomeric excesses. This diastereomeric resolution is very efficient for the preparation of optically pure δ-lactones.
ISSN:1345-8957
1347-3352
DOI:10.5650/jos.ess14124