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. ORCID: https://orcid.org/0000-0002-6453-7531, 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:	Schools > Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	Wiley
ISSN:	0947-6539
Date of First Compliant Deposit:	16 September 2020
Last Modified:	05 May 2023 07:18
URI:	https://orca.cardiff.ac.uk/id/eprint/74289

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