Stereochemistry of terpene derivatives. Part 3: Hydrolytic kinetic resolution as a convenient approach to chiral aminohydroxyiminocaranes with local anaesthetic activity

Abstract We have developed a stereoselective hydrolytic kinetic resolution process for diastereoisomeric mixtures of epoxyiminocarene intermediates in the presence of ( R , R )-(−)-(salen)Co(III)OAc catalyst, this was applied as the first step in the synthesis of novel chiral aminohydroxyiminocarane derivatives with local anaesthetic activity. The absolute configuration of the product was confirmed by X-ray crystallography.