Perfluoroalkylsulfonyl fluoride-mediated abnormal Beckmann rearrangement of steroid 17-oximes with acid-labile groups |
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| Authors: | Jinghan Gui Yun Wang Hailong Tian Yuqi Gao Weisheng Tian |
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| Affiliation: | 1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China;2. Shaanxi Engineering Center of Bioresource Chemistry and Sustainable Utilization, College of Science, Northwest A & F University, 3 Taicheng Road, Yangling, Shaanxi 712100, China |
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| Abstract: | A perfluoroalkylsulfonyl fluoride-mediated abnormal Beckmann rearrangement is reported which transforms steroid 17-oximes to the corresponding alkene nitriles regioselectively in good yields. This reaction is rapid (completes in 25 min), mild (proceeds at room temperature) and, most importantly, tolerates various acid-labile functional groups, such as methoxymethyl (MOM), ketal, and methyl enol ether, providing access to molecules that would be difficult to synthesize using existing methods. |
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| Keywords: | Perfluoroalkylsulfonyl fluoride Beckmann rearrangement Steroid 17-oxime Acid-labile group tolerance Quassin |
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