Development of the Ireland-Claisen rearrangement of alkoxy- and aryloxy-substituted allyl glycinates
Reference:
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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Official URL:
http://dx.doi.org/10.1021/jo1017124
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.
Details
| Item Type | Articles |
| Creators | Tellam, J. P.and Carbery, D. R. |
| DOI | 10.1021/jo1017124 |
| Departments | Faculty of Science > Chemistry |
| Refereed | Yes |
| Status | Published |
| ID Code | 22053 |
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