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

J P Tellam; Gabriele Kociok-Kohn; D R Carbery

doi:10.1021/ol802169j

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

J P Tellam, Gabriele Kociok-Kohn, D R Carbery

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

33 Citations (SciVal)

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 language	English
Pages (from-to)	5199-5202
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	22
DOIs	https://doi.org/10.1021/ol802169j
Publication status	Published - 2008

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10.1021/ol802169j

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title = "An Ireland-Claisen Approach to beta-Alkoxy alpha-Amino Acids",

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.",

author = "Tellam, \{J P\} and Gabriele Kociok-Kohn and Carbery, \{D R\}",

year = "2008",

doi = "10.1021/ol802169j",

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journal = "Organic Letters",

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AU - Tellam, J P

AU - Kociok-Kohn, Gabriele

AU - Carbery, D R

PY - 2008

Y1 - 2008

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/58149177445

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

U2 - 10.1021/ol802169j

DO - 10.1021/ol802169j

M3 - Article

SN - 1523-7060

VL - 10

SP - 5199

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JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

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

Abstract

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