Highly stereoselective formal [3 + 3] cycloaddition of enals and azomethine imines catalyzed by N-heterocyclic carbenes

Audrey Chan, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

268 Scopus citations

Abstract

N-Heterocyclic carbenes derived from N-mesityl benzimidazolium salts are effective catalysts for generating homoenolate species from α,β-unsaturated aldehydes. The nucleophilic intermediate adds to azomethine imines, and the resulting activated carbonyl unit undergoes an intramolecular acylation event. This formal [3 + 3] cycloaddition between α,β-unsaturated aldehydes and azomethine imines catalyzed by NHC has been developed to give substituted pyridazinones in good to excellent yields with high diastereoselectivity (>20:1). The NHC-catalyzed reaction accommodates aromatic and alkyl α,β-unsaturated aldehydes and various aromatic azomethine imines. The pyridazinones can undergo selective six-membered ring opening upon addition of alcohols or amines to give esters and amides.

Original languageEnglish (US)
Pages (from-to)5334-5335
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number17
DOIs
StatePublished - May 2 2007

ASJC Scopus subject areas

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

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