Investigations into the [2,3]-aza-Wittig rearrangement of N-alkyl N-allyl α-amino esters

Abstract

A Lewis acid is needed in order to allow the [2,3]-sigmatropic rearrangement of N-alkyl N-allyl α-amino esters to give rise to N-alkyl C-allyl glycine esters. Addition of iodomethane, rather than a Lewis acid, promotes quaternary ammonium salt formation, in situ ylide formation and [2,3]-sigmatropic rearrangement to N,N-dialkyl C-allyl glycine esters.