Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines

Siobhan Rose Smith, Charlene Fallan, James Edward Taylor, Ross Sinclair McLennan, David Sydney Bernard Daniels, Louis Christian Morrill, Alexandra Martha Zoya Slawin, Andrew David Smith

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30 Citations (Scopus)
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Abstract

A highly enantioselective Lewis base-catalysed formal [3+2] cycloaddition of ammonium enolates and oxaziridines to give stereodefined oxazolidin-4-ones in high yield is described. Employing an enantioenriched oxaziridine in this process leads to a matched/mis-matched effect with the isothiourea catalyst and allowed the synthesis of either syn- or anti-stereodefined oxazolidin-4-ones in high dr, yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks.
Original languageEnglish
Pages (from-to)10530–10536
JournalChemistry - A European Journal
Volume21
Issue number29
Early online date12 Jun 2015
DOIs
Publication statusPublished - 13 Jul 2015

Keywords

  • Organocatalysis
  • Nitrogen heterocycles
  • Oxygen heterocycles
  • Asymmetric synthesis

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