Literature DB >> 18928292

An Ireland-Claisen approach to beta-alkoxy alpha-amino acids.

James P Tellam1, Gabriele Kociok-Köhn, David R Carbery.   

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.

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Year:  2008        PMID： 18928292     DOI： 10.1021/ol802169j

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  4 in total

1.  Synthesis of the bridging framework of phragmalin-type limonoids.

Authors:  Terry P Lebold; Gary M Gallego; Christopher J Marth; Richmond Sarpong
Journal:  Org Lett       Date:  2012-04-03       Impact factor: 6.005

2.  Formation of Chiral Allylic Ethers via an Enantioselective Palladium-Catalyzed Alkenylation of Acyclic Enol Ethers.

Authors:  Harshkumar H Patel; Matthew B Prater; Scott O Squire; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2018-04-27       Impact factor: 15.419

3.  Global Diastereoconvergence in the Ireland-Claisen Rearrangement of Isomeric Enolates: Synthesis of Tetrasubstituted α-Amino Acids.

Authors:  Tyler J Fulton; Alexander Q Cusumano; Eric J Alexy; Yun E Du; Haiming Zhang; K N Houk; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2020-12-15       Impact factor: 15.419

4.  Gold-catalyzed reaction of oxabicyclic alkenes with electron-deficient terminal alkynes to produce acrylate derivatives.

Authors:  Yin-Wei Sun; Qin Xu; Min Shi
Journal:  Beilstein J Org Chem       Date:  2013-10-01       Impact factor: 2.883
  4 in total

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