Generation and reactivity of C(1)-ammonium enolates using isothiourea catalysis

Calum McLaughlin, Andrew D. Smith

Research output: Contribution to journalReview articlepeer-review

59 Citations (Scopus)
2 Downloads (Pure)

Abstract

C(1)-ammonium enolates are powerful, catalytically generated synthetic intermediates applied in the enantioselective α-functionalization of carboxylic acid derivatives. This review 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 utilizing two distinct catalyst turnover approaches.
Original languageEnglish
JournalChemistry - A European Journal
VolumeEarly View
Early online date10 Nov 2020
DOIs
Publication statusE-pub ahead of print - 10 Nov 2020

Keywords

  • Aryloxides
  • C(1)-ammonium enolates
  • Catalyst turnover
  • Formal cycloaddition
  • Isothioureas

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