Competition of the Addition/Cycloaddition Schemes in the Reaction Between Fluorinated Nitrones and Arylacetylenes:
Szymon Jarzyński1, Andrzej Krempiński2, Anna Pietrzak3
1Faculty of Chemistry, Department of Organic Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, Poland.
None:
The course of the reactions of acetylenes with fluorinated nitrones in the presence of Zn(OTf)2 and Et2Zn was investigated. The formation of hydroxylamines and/or 1,2-oxazolines as products was observed. The desired hydroxylamines were formed as main products if reactions were carried out with the usage of Et2Zn. In order to explain the obtained results, quantum mechanical calculations of the reaction paths leading to both products were carried out. Further research allowed us to develop the enantioselective variant of described reactions with the usage of enantiomerically pure AziPhenol ligand bearing chiral aziridine scaffold.
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