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

Smith, Siobhan R., Fallan, Charlene, Taylor, James E., McLennan, Ross, Daniels, David S. B., Morrill, Louis C., Slawin, Alexandra M. Z. and Smith, Andrew D. 2015. Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines. Chemistry - A European Journal 21 (29) , pp. 10530-10536. 10.1002/chem.201501271

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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 d.r., yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Wiley
ISSN: 0947-6539
Last Modified: 05 Feb 2020 15:46
URI: http://orca.cf.ac.uk/id/eprint/74289

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