Exploiting the Imidazolium Effect in Base-free Ammonium Enolate Generation: Synthetic and Mechanistic Studies

Claire M. Young, Daniel G. Stark, Thomas H. West, James E. Taylor, Andrew D. Smith

Research output: Contribution to journalArticle

20 Citations (Scopus)
40 Downloads (Pure)

Abstract

N-Acyl imidazoles and catalytic isothiourea hydrochloride salts function as ammonium enolate precursors in the absence of base. Enantioselective Michael addition–cyclization reactions using different α,β-unsaturated Michael acceptors have been performed to form dihydropyranones and dihydropyridinones with high stereoselectivity. Detailed mechanistic studies using RPKA have revealed the importance of the “imidazolium” effect in ammonium enolate formation and have highlighted key differences with traditional base-mediated processes.

Original languageEnglish
Pages (from-to)14394-14399
Number of pages6
JournalAngewandte Chemie - International Edition
Volume55
Issue number46
DOIs
Publication statusPublished - 7 Nov 2016

Keywords

  • imidazolium effect
  • isothiourea catalysis
  • mechanistic study
  • Michael addition
  • N-acyl imidazoles

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Exploiting the Imidazolium Effect in Base-free Ammonium Enolate Generation: Synthetic and Mechanistic Studies'. Together they form a unique fingerprint.

  • Profiles

    No photo of James Taylor

    James Taylor

    Person: Research & Teaching

    Cite this