Abstract
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.
| Original language | English |
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| Pages (from-to) | 7809-7821 |
| Number of pages | 13 |
| Journal | Journal of Organic Chemistry |
| Volume | 75 |
| Issue number | 22 |
| DOIs | |
| Publication status | Published - 19 Nov 2010 |