Generation and Reactivity of C(1)-Ammonium Enolates by Using Isothiourea Catalysis |
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Authors: | Calum McLaughlin Prof Andrew D Smith |
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Institution: | EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, Fife, KY16 9ST Scotland |
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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. |
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Keywords: | aryloxides C(1)-ammonium enolates catalyst turnover formal cycloaddition isothioureas |
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