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Exploiting the imidazolium effect in base-free ammonium enolate generation: synthetic and mechanistic studies

Research output: Contribution to journalArticle

Author(s)

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

School/Research organisations

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.
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Original languageEnglish
Pages (from-to)14394-14399
Number of pages6
JournalAngewandte Chemie International Edition
Volume55
Issue number46
Early online date20 Oct 2016
DOIs
Publication statusPublished - 7 Nov 2016

    Research areas

  • Imidazolium effect, Isothiourea catalysis, Mechanistic study , Michael addition, N-acyl imidazoles

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