Tellam, J. P. and Carbery, D. R., 2010. Development of the Ireland-Claisen rearrangement of alkoxy- and aryloxy-substituted allyl glycinates. Journal of Organic Chemistry, 75 (22), pp. 7809-7821.
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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.
|Item Type ||Articles|
|Creators||Tellam, J. P.and Carbery, D. R.|
|Departments||Faculty of Science > Chemistry|
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