title: 1,3-Dipolar cycloaddition of unstabilised azomethine ylides by Lewis base catalysis.
abstract: Lewis base catalysed 1,3-dipolar cycloaddition between α,β-unsaturated acyl fluorides and N-[(trimethylsilyl)methyl]amino ethers has been achieved using 1 mol% DMAP. Competition experiments and (19)F-NMR studies indicate that the cycloaddition occurs preferentially between the α,β-unsaturated acyl fluoride and the unstabilised azomethine ylide. In addition, an enantioselective variant, using chiral isothiourea catalysts, has been achieved with 14% ee.
authors.affiliation: Monash University, Clayton 3800, Melbourne, Australia.
authors.forename: Shveta
authors.initials: S
authors.lastname: Pandiancherri
authors.forename: Sarah J
authors.initials: SJ
authors.lastname: Ryan
authors.forename: David W
authors.initials: DW
authors.lastname: Lupton
mesh_terms: D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D058115:Lewis Bases / Q000737:chemistry*; D015394:Molecular Structure; D013882:Thiosemicarbazones / Q000138:chemical synthesis* / Q000737:chemistry; D013890:Thiourea / Q000031:analogs & derivatives / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D058115:Lewis Bases; D013882:Thiosemicarbazones; C512188:azomethine; D013890:Thiourea