The Ireland-Claisen rearrangement of 3-alkoxy- and 3-aryloxy-substituted allyl glycinates is presented. This [3,3]-sigmatropic rearrangement route offers direct access to syn -alkoxy and -aryloxy -amino acid systems. In particular, N,N-diboc glycine esters rearrange with excellent diastereoselectivities (dr 25:1). The synthesis of substrates, rearrangement optimization, and a discussion of stereoselection are presented.
Tellam, J. P., & Carbery, D. R. (2010). Development of the Ireland-Claisen rearrangement of alkoxy- and aryloxy-substituted allyl glycinates. Journal of Organic Chemistry, 75(22), 7809-7821. https://doi.org/10.1021/jo1017124