Literature DB >> 24867308

Organocatalytic Lewis base functionalisation of carboxylic acids, esters and anhydrides via C1-ammonium or azolium enolates.

Louis C Morrill1, Andrew D Smith.   

Abstract

This tutorial review highlights the organocatalytic Lewis base functionalisation of carboxylic acids, esters and anhydrides via C1-ammonium/azolium enolates. The generation and synthetic utility of these powerful intermediates is highlighted through their application in various methodologies including aldol-lactonisations, Michael-lactonisations/lactamisations and [2,3]-rearrangements.

Entities:  

Year:  2014        PMID: 24867308     DOI: 10.1039/c4cs00042k

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  24 in total

1.  Stereodivergent Allylic Substitutions with Aryl Acetic Acid Esters by Synergistic Iridium and Lewis Base Catalysis.

Authors:  Xingyu Jiang; Jason J Beiger; John F Hartwig
Journal:  J Am Chem Soc       Date:  2016-12-22       Impact factor: 15.419

2.  N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors:  Anna Lee; Karl A Scheidt
Journal:  Chem Commun (Camb)       Date:  2015-02-25       Impact factor: 6.222

3.  Traversing Steric Limitations by Cooperative Lewis Base/Palladium Catalysis: An Enantioselective Synthesis of α-Branched Esters Using 2-Substituted Allyl Electrophiles.

Authors:  Kevin J Schwarz; Colin M Pearson; Gabriel A Cintron-Rosado; Peng Liu; Thomas N Snaddon
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-18       Impact factor: 15.336

4.  CS2/CO2 Utilization Using Mukaiyama Reagent as a (Thio)carbonylating Promoter: A Proof-of-Concept Study.

Authors:  Abdussalam K Qaroush; Ala'a F Eftaiha; Amneh H Smadi; Khaleel I Assaf; Feda'a M Al-Qaisi; Fatima Alsoubani
Journal:  ACS Omega       Date:  2022-06-21

5.  Enantioselective α-Benzylation of Acyclic Esters Using π-Extended Electrophiles.

Authors:  Kevin J Schwarz; Chao Yang; James W B Fyfe; Thomas N Snaddon
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-20       Impact factor: 15.336

6.  Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines.

Authors:  Siobhan R Smith; Charlene Fallan; James E Taylor; Ross McLennan; David S B Daniels; Louis C Morrill; Alexandra M Z Slawin; Andrew D Smith
Journal:  Chemistry       Date:  2015-06-12       Impact factor: 5.236

7.  Enantioselective Synthesis of 3,5,6-Substituted Dihydropyranones and Dihydropyridinones using Isothiourea-Mediated Catalysis.

Authors:  Daniel G Stark; Louis C Morrill; David B Cordes; Alexandra M Z Slawin; Timothy J C O'Riordan; Andrew D Smith
Journal:  Chem Asian J       Date:  2015-11-12

8.  Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral.

Authors:  James J Douglas; Gwydion Churchill; Alexandra M Z Slawin; David J Fox; Andrew D Smith
Journal:  Chemistry       Date:  2015-09-25       Impact factor: 5.236

9.  Enantioselective Stereodivergent Nucleophile-Dependent Isothiourea-Catalysed Domino Reactions.

Authors:  Anastassia Matviitsuk; James E Taylor; David B Cordes; Alexandra M Z Slawin; Andrew D Smith
Journal:  Chemistry       Date:  2016-10-11       Impact factor: 5.236

10.  Enantioselective annulations for dihydroquinolones by in situ generation of azolium enolates.

Authors:  Anna Lee; Ashkaan Younai; Christopher K Price; Javier Izquierdo; Rama K Mishra; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2014-07-15       Impact factor: 15.419

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