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An Ireland-Claisen Approach to beta-Alkoxy alpha-Amino Acids


Reference:

Tellam, J. P., Kociok-Kohn, G. and Carbery, D. R., 2008. An Ireland-Claisen Approach to beta-Alkoxy alpha-Amino Acids. Organic Letters, 10 (22), pp. 5199-5202.

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Official URL:

http://dx.doi.org/10.1021/ol802169j

Abstract

A diastereoselective Ireland-Claisen approach to beta-alkoxy alpha-amino acid esters is reported. Amino acid esters of enol ethereal allylic alcohols undergo facile syn-selective [3,3]-sigmatropic rearrangement via silyl ketene acetals. Substrate synthesis, rearrangement development, stereoselectivity, and product elaboration are discussed.

Details

Item Type Articles
CreatorsTellam, J. P., Kociok-Kohn, G. and Carbery, D. R.
DOI10.1021/ol802169j
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code12343

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