PRODUCTION OF DELTA-LACTONES OF DIASTEREOMER HYDROXYCARBOXYLIC ACID AMIDES

摘要

PROBLEM TO BE SOLVED: To produce an optically activeδ-lactone in high selectively and simply from a diastereomer amide obtained by reacting an optical isomer mixture of aδ-lactone with an optically active phenylethylamine. SOLUTION: An optical isomer mixture of aδ-lactone of formula I (R is a 3-7C straight-chain hydrocarbon group) (in the case of racemic modification, preferably (±)-δ-nonalactone and (±)-δ-decalactone) is reacted with an optically active phenylethylamine of formula II as a reagent for optical resolution to give a diastereomer hydroxycarboxylic acid amide [preferably N-(1- phenylethyl)-5-hydroxynonanoic acid amide] of formula III. The compound is hydrolyzed, subjected to ring formation reaction in the presence of sulfonic acid or directly subjected to ring formation reaction in the presence of an acid to give an optically active substance of aδ-lactone of formula I.