Asymmetric Isothiourea‐Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines. Issue 29 (12th June 2015)

• Record Type: Journal Article
• Authors: Smith, Siobhan R.; Fallan, Charlene; Taylor, James E.; McLennan, Ross; Daniels, David S. B.; Morrill, Louis C.; Slawin, Alexandra M. Z.; Smith, Andrew D.
• Is Part Of: Chemistry. Volume 21:Issue 29(2015)
• Page Start: 10530
• Page End: 10536
• Publication Date: 2015-06-12
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201501271
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 <italic>syn‐</italic> or <italic>anti</italic>‐stereodefined oxazolidin‐4‐ones in high d.r., yield and <italic>ee</italic>. Additionally, the oxazolidin‐4‐one products have been derivatised to afford functionalised enantioenriched building blocks.</p> </abstract>