Thiazolium-catalyzed additions of acylsilanes: A general strategy for acyl anion addition reactions

Anita E. Mattson, Ashwin R. Bharadwaj, Andrea M. Zuhl, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticle

117 Scopus citations

Abstract

A strategy utilizing N-heterocyclic carbenes (NHCs) derived from thiazolium salts has been developed for the generation of carbonyl anions from acylsilanes. Synthetically useful 1,4-diketones and N-phosphinoyl-α- aminoketones have been prepared in good to excellent yields via NHC-catalyzed additions of acylsilanes to the corresponding α,β-unsaturated systems and N-phosphinoylimines. These organocatalytic reactions are air- and water-tolerant methods to execute robust carbonyl anion addition reactions. Additionally, polysubstituted aromatic furans and pyrroles have been efficiently synthesized in a one-pot process using this carbonyl anion methodology. The addition of alcohols to the reaction renders the process catalytic in thiazolium salt. In an effort to synthesize a potential intermediate along the proposed reaction pathway, silylated thiazolium carbinols have been identified to provide good yields of carbonyl anion addition products when subjected to the standard reaction conditions in the presence of suitable electrophiles.

Original languageEnglish (US)
Pages (from-to)5715-5724
Number of pages10
JournalJournal of Organic Chemistry
Volume71
Issue number15
DOIs
StatePublished - Jul 21 2006

ASJC Scopus subject areas

  • Organic Chemistry

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