Decarboxylative rearrangement of an alkanoyl arylcarbonyl peroxide involving migration of a primary chiral centre

Abstract

Although migration of a secondary chiral centre in the decarboxylative rearrangement of diacyl peroxides occurs with retention of configuration, this is not the case for migration of the primary chiral centre in (2S)-O-ethyl-N-trifluoroacetyl-β-aspartyl m-chlorobenzoyl peroxide (2). This result is in keeping with the suggestion that the mechanisms of the reactions are different and that the latter rearrangement proceeds via a radical cage process.