Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 5, Pages 1533-1555Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202002059
Keywords
aryloxides; C(1)-ammonium enolates; catalyst turnover; formal cycloaddition; isothioureas
Categories
Funding
- EPSRC [EP/M508214/1]
- Royal Society
- EPSRC [1792153] Funding Source: UKRI
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Ammonium enolates are powerful synthetic intermediates generated catalytically using isothiourea Lewis base organocatalysts, and have been applied in selective alpha-functionalisation reactions with various precursors. Their utility in intra- and intermolecular C-C and C-X bond forming processes with electrophiles is showcased using different catalyst turnover approaches.
C(1)-Ammonium enolates are powerful, catalytically generated synthetic intermediates applied in the enantioselective alpha-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, alpha-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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