Literature DB >> 32557875

Generation and Reactivity of C(1)-Ammonium Enolates by Using Isothiourea Catalysis.

Calum McLaughlin1, Andrew D Smith1.   

Abstract

C(1)-Ammonium enolates are powerful, catalytically generated synthetic intermediates applied in the enantioselective α-functionalisation of carboxylic acid derivatives. This minireview describes the recent developments in the generation and application of C(1)-ammonium enolates from various precursors (carboxylic acids, anhydrides, acyl imidazoles, aryl esters, α-diazoketones, alkyl halides) using isothiourea Lewis base organocatalysts. Their synthetic utility in intra- and intermolecular enantioselective C-C and C-X bond forming processes on reaction with various electrophiles will be showcased utilising two distinct catalyst turnover approaches.
© 2020 The Authors. Published by Wiley-VCH GmbH.

Entities:  

Keywords:  C(1)-ammonium enolates; aryloxides; catalyst turnover; formal cycloaddition; isothioureas

Year:  2020        PMID: 32557875     DOI: 10.1002/chem.202002059

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  6 in total

1.  Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane.

Authors:  David Weinzierl; Mario Waser
Journal:  Beilstein J Org Chem       Date:  2021-04-08       Impact factor: 2.883

2.  Solvent directed chemically divergent synthesis of β-lactams and α-amino acid derivatives with chiral isothiourea.

Authors:  Dong-Sheng Ji; Hui Liang; Kai-Xuan Yang; Zhi-Tao Feng; Yong-Chun Luo; Guo-Qiang Xu; Yucheng Gu; Peng-Fei Xu
Journal:  Chem Sci       Date:  2022-01-18       Impact factor: 9.825

3.  Cooperative Palladium/Isothiourea Catalyzed Enantioselective Formal (3+2) Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Esters.

Authors:  Jacqueline Bitai; Alastair J Nimmo; Alexandra M Z Slawin; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-28       Impact factor: 16.823

4.  A Desilylative Approach to Alkyl Substituted C(1)-Ammonium Enolates: Application in Enantioselective [2+2] Cycloadditions.

Authors:  Yihong Wang; Claire M Young; Honglei Liu; Will C Hartley; Max Wienhold; David B Cordes; Alexandra M Z Slawin; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-08       Impact factor: 16.823

5.  Lewis Base Catalyzed Synthesis of Sulfur Heterocycles via the C1-Pyridinium Enolate.

Authors:  Simon Cromwell; Randy Sutio; Changhe Zhang; Georgina K Such; David W Lupton
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-11       Impact factor: 16.823

6.  Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions.

Authors:  Lotte Stockhammer; David Weinzierl; Thomas Bögl; Mario Waser
Journal:  Org Lett       Date:  2021-07-28       Impact factor: 6.005

  6 in total

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