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Silver‐Catalyzed Cyclization of Propargylic Amides to Oxazolines
Author(s) -
Wong Valerie H. L.,
White Andrew J. P.,
Hor T. S. Andy,
Hii King Kuok Mimi
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500610
Subject(s) - chemistry , catalysis , selectivity , alkyne , ligand (biochemistry) , combinatorial chemistry , organic chemistry , medicinal chemistry , receptor , biochemistry
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 NH 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.