Competition of the Addition/Cycloaddition Schemes in the Reaction Between Fluorinated Nitrones and Arylacetylenes: Comprehensive Experimental and DFT Study

氟代硝酮与芳基乙炔反应中加成/环加成机制的竞争:全面的实验和DFT研究

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Abstract

The course of the reactions of acetylenes with fluorinated nitrones in the presence of Zn(OTf)(2) and Et(2)Zn 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 Et(2)Zn. 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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