Direct amination of homoenolates catalyzed by N-heterocyclic carbenes

Audrey Chan, Karl A. Scheidt

Research output: Contribution to journalArticlepeer-review

147 Scopus citations

Abstract

N-Heterocyclic carbenes derived from N-mesityl-N-methyltriazolium salts are effective catalysts for generating homoenolate species from α,β-unsaturated aldehydes. The unique intermediate adds to the electrophilic nitrogen of 1-acyl-2-aryldiazenes, and the resulting activated carbonyl unit undergoes an intramolecular acylation event. This formal [3+2] cycloaddition between α,β-unsaturated aldehydes and acylaryldiazenes, catalyzed by an N-heterocyclic carbene, produces substituted pyrazolidinones in good yields. This new NHC-catalyzed reaction accommodates aromatic and alkyl α,β-unsaturated aldehydes and various aromatic diazenes. A chiral triazolium salt catalyzes the formation of the pyrazolidinone product in moderate yield and good enantioselectivity. The pyrazolidinones can undergo reductive N-N bond cleavage to give β-amino acid derivatives.

Original languageEnglish (US)
Pages (from-to)2740-2741
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number9
DOIs
StatePublished - Mar 5 2008

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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