Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines

Siobhan R. Smith, Charlene Fallan, James E. Taylor, Ross McLennan, David S.B. Daniels, Louis C. Morrill, Alexandra M.Z. Slawin, Andrew D. Smith

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24 Citations (Scopus)

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 d.r., 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
Number of pages7
JournalChemistry - A European Journal
Volume21
Issue number29
Early online date12 Jun 2015
DOIs
Publication statusPublished - 1 Jul 2015

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Keywords

  • asymmetric synthesis
  • heterocycles
  • Lewis base
  • organocatalysis
  • oxaziridines

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Smith, S. R., Fallan, C., Taylor, J. E., McLennan, R., Daniels, D. S. B., Morrill, L. C., ... Smith, A. D. (2015). Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines. Chemistry - A European Journal, 21(29), 10530-10536. https://doi.org/10.1002/chem.201501271