A highly efficient free radical approach to trisubstituted pyrrolidinones

Abstract

The radical-mediated cyclisation of serine derived α-chloroamides has been found to be influenced in both yield and stereoselectivity by the nature of the substituent at the site of radical generation—radicals substituted at the α-position by methyl, phenyl and dichloro groups underwent smooth cyclisation to give excellent yield of pyrrolidinones in which the trans-C-2: C-3 isomer predominated—this procedure has potential application to a new synthesis of the kainoid amino acids.