Literature DB >> 30070858

Stereodivergence in the Ireland-Claisen Rearrangement of α-Alkoxy Esters.

Maša Podunavac1, Jacob J Lacharity1, Kerry E Jones1, Armen Zakarian1.   

Abstract

A systematic investigation into the Ireland-Claisen rearrangement of α-alkoxy esters is reported. In all cases, the use of KN(SiMe3)2 in toluene gave rearrangement products corresponding to a Z-enolate intermediate with excellent diastereoselectivity, presumably because of chelation control. On the other hand, chelation-controlled enolate formation could be overcome for most substrates through the use of lithium diisopropylamide (LDA) in tetrahydrofuran (THF).

Entities:  

Year:  2018        PMID： 30070858     DOI： 10.1021/acs.orglett.8b02011

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


  3 in total

1.  Scalable Total Synthesis, IP3R Inhibitory Activity of Desmethylxestospongin B, and Effect on Mitochondrial Function and Cancer Cell Survival.

Authors:  Maša Podunavac; Artur K Mailyan; Jeffrey J Jackson; Alenka Lovy; Paula Farias; Hernan Huerta; Jordi Molgó; Cesar Cardenas; Armen Zakarian
Journal:  Angew Chem Int Ed Engl       Date:  2021-04-08       Impact factor: 15.336

2.  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

3.  Optically Pure Aziridin-2-yl Methanols as Readily Available 1H NMR Sensors for Enantiodiscrimination of α-Racemic Carboxylic Acids Containing Tertiary or Quaternary Stereogenic Centers.

Authors:  Martyna Malinowska; Szymon Jarzyński; Adam Pieczonka; Michał Rachwalski; Stanisław Leśniak; Anna Zawisza
Journal:  J Org Chem       Date:  2020-09-02       Impact factor: 4.354
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.