Silver-catalyzed cyclization of propargylic amides to oxazolines
File(s)
Accepted version
Author(s)
Wong, VHL
White, AJP
Hor, TSA
Hii, KKM
Type
Journal Article
Abstract
A ligand-accelerated effect is observed in the cyclization of propargylic amides catalyzed by bis(pyridyl)silver(I) complexes, with an unexpected reversal of electronic demand to the analogous N[BOND]H addition reaction. The catalyst was found to be effective for internal alkyne substrates, offering exclusive selectivity for the 5-exo-dig product. Differences in selectivity profile between gold- and silver-catalyzed processes are highlighted and discussed.
Date Issued
2015-11-25
Date Acceptance
2015-11-25
Citation
Advanced Synthesis & Catalysis, 2015, 357 (18), pp.3943-3948
ISSN
1615-4169
Publisher
Wiley-VCH Verlag
Start Page
3943
End Page
3948
Journal / Book Title
Advanced Synthesis & Catalysis
Volume
357
Issue
18
Copyright Statement
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: Wong, V. H. L., White, A. J. P., Hor, T. S. and Hii, K. K. (2015), Silver-Catalyzed Cyclization of Propargylic Amides to Oxazolines. Adv. Synth. Catal., 357: 3943–3948, which has been published in final form at http://dx.doi.org/10.1002/adsc.201500610.
Subjects
Science & Technology
Physical Sciences
Chemistry, Applied
Chemistry, Organic
Chemistry
cyclization
heterocycles
oxazolines
silver
N-PROPARGYLAMIDES
GOLD CATALYSIS
CYCLOISOMERIZATION
SELECTIVITY
COMPLEXES
Organic Chemistry
0305 Organic Chemistry
0904 Chemical Engineering
0302 Inorganic Chemistry
Publication Status
Published