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Direct Synthesis of 4-Fluoroisoxazoles through Gold-Catalyzed Cascade Cyclization-Fluorination of 2-Alkynone O-Methyl Oximes

Yunkyung Jeong, Bom-I Kim, Jae Kyun Lee and Jae-Sang Ryu*

*College of Pharmacy & Graduate School of Pharmaceutical Sciences, Ewha Womans University, 11-1 Daehyun-Dong, Seodaemun-Gu, Seoul 120-750, Republic of Korea, Email: ryujewha.ac.kr

Y. Jeong, B.-I Kim, J. K. Lee, J.-S. Ryu, J. Org. Chem., 2014, 79, 6444-6455.

DOI: 10.1021/jo5008702 (free Supporting Information)


Abstract

A catalytic intramolecular cyclization of 2-alkynone O-methyl oximes and subsequent fluorination proceeds smoothly at room temperature in the presence of 5 mol % of (IPr)AuCl, 5 mol % of AgOTs, 2.5 equiv of Selectfluor, and 2 equiv of NaHCO3. This process features an efficient one-pot cascade route to fluoroisoxazoles with high yields and high selectivity under mild reaction conditions.


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Key Words

Isoxazoles, Selectfluor


ID: J42-Y2014