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

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 cata... Full description

Journal Title: Chemistry: A European Journal July 2015, Vol.21(29), pp.10530-10536
Main Author: Smith, Siobhan
Other Authors: Fallan, Charlene , Taylor, James , Mclennan, Ross , Daniels, David , Morrill, Louis , Slawin, Alexandra , Smith, Andrew
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201501271
Link: http://search.proquest.com/docview/1786201487/?pq-origsite=primo
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title: Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines
format: Article
creator:
  • Smith, Siobhan
  • Fallan, Charlene
  • Taylor, James
  • Mclennan, Ross
  • Daniels, David
  • Morrill, Louis
  • Slawin, Alexandra
  • Smith, Andrew
subjects:
  • Cycloaddition
  • Formations
  • Asymmetry
  • Catalysts
  • Synthesis
  • Analysis (MD)
  • Chemical Analysis (Ep)
  • Chemical Analysis (Ed)
  • Chemical Analysis (EC)
ispartof: Chemistry: A European Journal, July 2015, Vol.21(29), pp.10530-10536
description: 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. Choose your partner: An asymmetric isothiourea-catalysed [3+2] formal cycloaddition of homoanhydrides and oxaziridines for the formation of stereodefined oxazolidin-4-ones in high yields and with high enantioselectivities is described (see scheme). The use of racemic and enantioenriched oxaziridines is studied, leading to the observation of a matched/mismatched effect between the catalyst and the oxaziridine.
language: eng
source:
identifier: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201501271
fulltext: fulltext
issn:
  • 09476539
  • 0947-6539
  • 15213765
  • 1521-3765
url: Link


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titleAsymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines
creatorSmith, Siobhan ; Fallan, Charlene ; Taylor, James ; Mclennan, Ross ; Daniels, David ; Morrill, Louis ; Slawin, Alexandra ; Smith, Andrew
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subjectCycloaddition ; Formations ; Asymmetry ; Catalysts ; Synthesis ; Analysis (MD) ; Chemical Analysis (Ep) ; Chemical Analysis (Ed) ; Chemical Analysis (EC)
descriptionA 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. Choose your partner: An asymmetric isothiourea-catalysed [3+2] formal cycloaddition of homoanhydrides and oxaziridines for the formation of stereodefined oxazolidin-4-ones in high yields and with high enantioselectivities is described (see scheme). The use of racemic and enantioenriched oxaziridines is studied, leading to the observation of a matched/mismatched effect between the catalyst and the oxaziridine.
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titleAsymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines
descriptionA 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. Choose your partner: An asymmetric isothiourea-catalysed [3+2] formal cycloaddition of homoanhydrides and oxaziridines for the formation of stereodefined oxazolidin-4-ones in high yields and with high enantioselectivities is described (see scheme). The use of racemic and enantioenriched oxaziridines is studied, leading to the observation of a matched/mismatched effect between the catalyst and the oxaziridine.
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titleAsymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines
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abstractA 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. Choose your partner: An asymmetric isothiourea-catalysed [3+2] formal cycloaddition of homoanhydrides and oxaziridines for the formation of stereodefined oxazolidin-4-ones in high yields and with high enantioselectivities is described (see scheme). The use of racemic and enantioenriched oxaziridines is studied, leading to the observation of a matched/mismatched effect between the catalyst and the oxaziridine.
doi10.1002/chem.201501271
urlhttp://search.proquest.com/docview/1786201487/
date2015-07-13