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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
CreatorsTellam, J. P.and Carbery, D. R.
DOI10.1021/jo1017124
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code22053

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