Premium
Ligand Effect and Control of E ‐ and Z ‐Selectivity in the Silver‐Catalyzed Synthesis of 4‐Bromooxazolines
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.201500157
Subject(s) - hydroamination , chemistry , ligand (biochemistry) , catalysis , intramolecular force , stereoselectivity , stereospecificity , selectivity , electronic effect , stereochemistry , chiral ligand , combinatorial chemistry , medicinal chemistry , organic chemistry , enantioselective synthesis , receptor , biochemistry
The stereospecific intramolecular hydroamination of alkynyl trichloroacetimidates catalyzed by bis(pyridyl)silver(I) complexes to form 1,3‐oxazolines and oxazines has been investigated in greater detail. The rate of the reaction is profoundly influenced by the electronic character of the pyridyl ligand; leading to optimized conditions whereby reactions can be completed at ambient temperature with catalyst loadings as low as 1 mol%, while maintaining stereoselectivity towards the ( Z )‐isomer. Further investigations into establishing the role of the ligand, and the synthesis of ( E )‐isomer, are also presented.