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

Title
Direct Synthesis of 4-Fluoroisoxazoles through Gold-Catalyzed Cascade Cyclization-Fluorination of 2-Alkynone O-Methyl Oximes
Authors
정윤경김봄이이재균류재상
Keywords
2-Alkynone O-Methyl Oximes; Gold-Catalyzed; Direct Synthesis; 4-Fluoroisoxazoles
Issue Date
2014-06
Publisher
Journal of organic chemistry
Citation
VOL 79, NO 14, 6444-6455
Abstract
A tandem protocol for the synthesis of fluorinated isoxazoles has been developed via catalytic intramolecular cyclizations of 2-alkynone O-methyl oximes and ensuing fluorination. The reactions proceed 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.
URI
http://pubs.kist.re.kr/handle/201004/48639
ISSN
00223263
Appears in Collections:
KIST Publication > Article
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