Alpha- and Beta-Prodine Type Compounds: Configurational Studies

Abstract

Abstract The addition of various lithium aryl compounds to 1:3-dimethyl-4-piperidone is investigated. Those stereoisomers present as the major proportion of the respective stereoisomeric mixtures are shown to have similar infra-red absorption characteristics which are different from those exhibited by those isomers formed in minor amount. The stereochemistry of addition to 6-membered alicyclic and heterocyclic ketones is discussed; on the basis of these discussions, and the rates of hydrolysis of appropriate esters, the above isomers formed in major amount are allocated the trans (Me/Ar) configuration. The analgesic activities in mice of various stereoisomeric amino-alcohols and esters are given.