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

I Coldham, ML Middleton, PL Taylor

Index: Coldham, Iain; Middleton, Mark L.; Taylor, Philip L. Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 17 p. 2817 - 2821

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Citation Number: 29

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.

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