Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones

Pei-Pei Yeh, David Sydney Bernard Daniels, Charlene Fallan, Eoin Rory Gould, Carmen Simal Fernandez, James Edward Taylor, Alexandra Martha Zoya Slawin, Andrew David Smith

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36 Citations (Scopus)
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Abstract

The exploration and expansion of the scope of the isothiourea-mediated synthesis of dihydropyridinones is presented. The use of ketimines derived from α,β-unsaturated γ-ketoesters as the Michael acceptor in a Michael addition / lactamisation cascade gives access to a range of dihydropyridinones with high enantioselectivity. The nature of the N-sulfonyl group present on the ketimine is extensively investigated, with further studies into derivatisation of the dihydropyridinone core also reported.
Original languageEnglish
Pages (from-to)2177-2191
JournalOrganic & Biomolecular Chemistry
Volume13
Issue number7
Early online date2 Jan 2015
DOIs
Publication statusPublished - 21 Feb 2015

Keywords

  • Derivatisation
  • High enantioselectivity
  • Isothiourea
  • Ketimines
  • Keto ester
  • Michael acceptors
  • Michael additions
  • Sulfonyl groups

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