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

Research output: Contribution to journalArticle

25 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)5199-5202
Number of pages4
JournalOrganic Letters
Volume10
Issue number22
DOIs
Publication statusPublished - 2008

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Ireland
amino acids
esters
Esters
Amino Acids
Stereoselectivity
acetals
Acetals
alcohols
Substrates
synthesis
products
alkoxyl radical
ketene
allyl alcohol

Cite this

An Ireland-Claisen Approach to beta-Alkoxy alpha-Amino Acids. / Tellam, J P; Kociok-Kohn, Gabriele; Carbery, D R.

In: Organic Letters, Vol. 10, No. 22, 2008, p. 5199-5202.

Research output: Contribution to journalArticle

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