ASYMMETRIC INDUCTION IN THE FREE-RADICAL ADDITION OF THIOLACETIC ACID TO DI-l-MENTHYL MALEATE AND DI-l-MENTHYL FUMARATE

Abstract

Numerous studies of asymmetric inductions via ionic processes have been reported;¹ however, there have been few examples via free-radical processes.² Recently, we were successful in observing asymmetric induction in free-radical additions of thiolacetic acid to cyclohexanone and also to Z-2-octene in l-menthol^3,4 and of menthyl mercaptoacetate to prochiral olefins^5,6 (enantiofacial differentiation) and radical addition of achiral thiols to l-menthyl crotonate and l-menthyl methacrylate^7,8 (diastereofacial differentiation).