1,3-dipolar cycloaddition of unstabilised azomethine ylides by lewis base catalysis

Shveta Pandiancherri, Sarah J Ryan, David Lupton

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36 Citations (Scopus)

Abstract

Lewis base catalysed 1,3-dipolar cycloaddition between alpha,beta-unsaturated acyl fluorides and N-[(trimethylsilyl)methyl]amino ethers has been achieved using 1 mol DMAP. Competition experiments and 19F-NMR studies indicate that the cycloaddition occurs preferentially between the alpha,beta-unsaturated acyl fluoride and the unstabilised azomethine ylide. In addition, an enantioselective variant, using chiral isothiourea catalysts, has been achieved with 14 ee.
Original languageEnglish
Pages (from-to)7903 - 7911
Number of pages9
JournalOrganic & Biomolecular Chemistry
Volume10
Issue number39
DOIs
Publication statusPublished - 2012

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