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Catalytic Three-Component Domino Reaction for the Preparation of Trisubstituted Oxazoles.

von Wachenfeldt, Henrik LU ; Röse, Philipp ; Paulsen, Filip ; Loganathan, Nagarajan LU and Strand, Daniel LU (2013) In Chemistry: A European Journal 19(24). p.7982-7988
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.
Please use this url to cite or link to this publication:
author
; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Chemistry: A European Journal
volume
19
issue
24
pages
7982 - 7988
publisher
Wiley-Blackwell
external identifiers
  • wos:000319825500039
  • pmid:23592540
  • scopus:84878534854
  • pmid:23592540
ISSN
1521-3765
DOI
10.1002/chem.201300019
language
English
LU publication?
yes
id
2a326523-90c3-476c-ac99-a821e698e73e (old id 3733701)
date added to LUP
2016-04-01 10:51:27
date last changed
2025-10-14 10:00:05
@article{2a326523-90c3-476c-ac99-a821e698e73e,
  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.}},
  author       = {{von Wachenfeldt, Henrik and Röse, Philipp and Paulsen, Filip and Loganathan, Nagarajan and Strand, Daniel}},
  issn         = {{1521-3765}},
  language     = {{eng}},
  number       = {{24}},
  pages        = {{7982--7988}},
  publisher    = {{Wiley-Blackwell}},
  series       = {{Chemistry: A European Journal}},
  title        = {{Catalytic Three-Component Domino Reaction for the Preparation of Trisubstituted Oxazoles.}},
  url          = {{http://dx.doi.org/10.1002/chem.201300019}},
  doi          = {{10.1002/chem.201300019}},
  volume       = {{19}},
  year         = {{2013}},
}