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

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 precurso...

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Detalles Bibliográficos
Autores principales: McLaughlin, Calum, Smith, Andrew D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7894297/
https://www.ncbi.nlm.nih.gov/pubmed/32557875
http://dx.doi.org/10.1002/chem.202002059
Descripción
Sumario: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.