TY - JOUR
T1 - Catalytic Three-Component Domino Reaction for the Preparation of Trisubstituted Oxazoles.
AU - von Wachenfeldt, Henrik
AU - Röse, Philipp
AU - Paulsen, Filip
AU - Loganathan, Nagarajan
AU - Strand, Daniel
PY - 2013
Y1 - 2013
N2 - 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.
AB - 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.
U2 - 10.1002/chem.201300019
DO - 10.1002/chem.201300019
M3 - Article
C2 - 23592540
SN - 1521-3765
VL - 19
SP - 7982
EP - 7988
JO - Chemistry: A European Journal
JF - Chemistry: A European Journal
IS - 24
ER -