title: Catalytic three-component domino reaction for the preparation of trisubstituted oxazoles.
abstract: Multicomponent reactions are attractive for assembling functionalized heterocyclic compounds. To this end, an efficient gold-catalyzed three-component domino reaction to form oxazoles directly from imines, alkynes, and acid chlorides is presented. The reaction proceeds in a single synthetic step by using a gold(III)-N,N'-ethylenebis(salicylimine) (salen) catalyst to give trisubstituted oxazoles in up to 96 % yield. The substrate scope, a mechanistic study exploring the role of the gold catalyst, and the synthetic applications of the oxazole products are discussed.
authors.affiliation: Centre for Analysis and Synthesis, Department of Chemistry, Lund University, PO Box 124, 22100 Lund, Sweden.
authors.forename: Henrik v
authors.initials: Hv
authors.lastname: Wachenfeldt
authors.forename: Philipp
authors.initials: P
authors.lastname: Röse
authors.forename: Filip
authors.initials: F
authors.lastname: Paulsen
authors.forename: Nagarajan
authors.initials: N
authors.lastname: Loganathan
authors.forename: Daniel
authors.initials: D
authors.lastname: Strand
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006046:Gold / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D007097:Imines; D010080:Oxazoles; D006046:Gold