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 language | English |
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Pages (from-to) | 10530-10536 |
Number of pages | 7 |
Journal | Chemistry - A European Journal |
Volume | 21 |
Issue number | 29 |
Early online date | 12 Jun 2015 |
DOIs | |
Publication status | Published - 1 Jul 2015 |
Keywords
- asymmetric synthesis
- heterocycles
- Lewis base
- organocatalysis
- oxaziridines
ASJC Scopus subject areas
- General Chemistry