Generation and Reactivity of C(1)‐Ammonium Enolates by Using Isothiourea Catalysis
Calum McLaughlin, Andrew D. Smith
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.
Topics & Concepts
Enantioselective synthesisElectrophileChemistryCatalysisLewis acids and basesAlkylOrganic chemistryAmmoniumArylHalideReactivity (psychology)Combinatorial chemistryIntermolecular forceMoleculeMedicineAlternative medicinePathologyAsymmetric Synthesis and CatalysisCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions