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

  • Andrew David Smith (Creator)
  • Claire Mary Young (Contributor)
  • Daniel Graham Stark (Contributor)
  • Thomas Henry West (Contributor)
  • James Edward Taylor (Contributor)



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.
Date made available17 Aug 2016
PublisherUniversity of St Andrews

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