Title

Diastereoselective Heterocyclization of Geminal Bromo-fluoro Arylcyclopropanes by Nitrosonium Tetrafluoroborate: Access to 4-fluorinated Isoxazolines and Isoxazoles

Document Type

Article

Publication Date

11-2019

Keywords

2-Aryl-1-bromo-1-fluorocyclopropanes, Nitrosonium tetrafluoroborate, 5-Aryl-4-bromo-4-fluoroisoxazolines, 5-Aryl-4-fluoroisoxazoles

Organizational Units

College of Natual Science and Mathematics, Chemistry and Biochemistry

Abstract

A series of 5-aryl-4-bromo-4-fluoroisoxazolines was synthesized via nitrosation of 2-aryl-1-bromo-1-fluorocyclopropanes with NOBF4. It was shown that the E-isomers of the cyclopropanes react highly regio- and diastereoselectively leading exclusively to the E-isomers of the isoxazolines. The obtained 5-aryl-4-bromo-4-fluoroisoxazolines were transformed selectively into the corresponding 5-aryl-4-fluoro- or 5-aryl-4-bromoisoxazoles in good yields in the reaction with Lewis acids.

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