Premium
Catalytic Three‐Component Domino Reaction for the Preparation of Trisubstituted Oxazoles
Author(s) -
Wachenfeldt Henrik v.,
Röse Philipp,
Paulsen Filip,
Loganathan Nagarajan,
Strand Daniel
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300019
Subject(s) - oxazole , catalysis , yield (engineering) , domino , combinatorial chemistry , chemistry , substrate (aquarium) , cascade reaction , reaction conditions , component (thermodynamics) , organic chemistry , materials science , oceanography , physics , metallurgy , thermodynamics , geology
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.