The oxyallyl cation in synthesis: preparation of analogues of cocaine

Abstract

An attempt has been made to establish the synthetic utility of cycloaddition reactions involving the oxyallyl cation [graphic omitted]. Reactions of this intermediate (R¹,R³= alkyl; R²,R⁴= H; and M = Na) with furan and N-methylpyrrole were particularly facile, and have been used for the synthesis of a number of novel analogues of cocaine. Although some of the cycloaddition products have been reported by other workers, there has always been a paucity of experimental details. We provide herein full experimental details for our reactions, and also a tabular survey of methods used and results obtained.