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

Authors

Oksana B. Bondarenko, Lomonosov Moscow State University
Arseniy I. Komarov, Lomonosov Moscow State University
George L. Karetnikov, Lomonosov Moscow State University
Svetlana N. Nikolaeva, Lomonosov Moscow State University
Nikolai V. Zyk, Lomonosov Moscow State University
Tina Holt, University of Denver
Andrei G. Kutateladze, University of DenverFollow

Publication Date

11-2019

Document Type

Article

Organizational Units

College of Natual Science and Mathematics, Chemistry and Biochemistry

Keywords

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

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.

Publication Statement

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Recommended Citation

Bondarenko, O. B., Komarov, A. I., Karetnikov, G. L., Nikolaeva, S. N., Zyk, N. V., Holt, T., & Kutateladze, A. G. (2019). Diastereoselective heterocyclization of geminal bromo-fluoro arylcyclopropanes by nitrosonium tetrafluoroborate: Access to 4-fluorinated isoxazolines and isoxazoles. Tetrahedron, 75(46), 130666. DOI: 10.1016/j.tet.2019.130666.