Synthesis of 4-Isoxazolines through Gold(I)-Catalyzed Cyclization of Propargylic N-Hydroxylamines

B. Chandrasekhar, Sewon Ahn and Jae-Sang Ryu*

*College of Pharmacy & Graduate School of Pharmaceutical Sciences, Ewha Womans University, 52 Ewhayeodae-gil, Seodaemun-Gu, Seoul 03760, Republic of Korea, Email: ryujewha.ac.kr

B. Chandrasekhar, S. Ahn, J.-S. Ryu, J. Org. Chem., 2016, 81, 6740-6749.

DOI: 10.1021/acs.joc.6b01499

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Abstract

Intramolecular cyclizations of propargylic N-hydroxylamines provide 4-isoxazolines rapidly at room temperature in the presence of 5 mol % (PPh₃)AuCl/5 mol % AgOTf or 5 mol % (PPh₃)AuNTf₂. This process offers high yields, short reaction times, and mild reaction conditions.

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Key Words

4-isoxazolines

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ID: J42-Y2016