Perfluoroalkylsulfonyl fluoride-mediated abnormal Beckmann rearrangement of steroid 17-oximes with acid-labile groups
2014
Gui, Jinghan | Wang, Yun | Tian, Hailong | Gao, Yuqi | Tian, Weisheng
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 25min), 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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书目信息
Tetrahedron letters
卷
55
期
30
页码
4233
- 4235
ISSN
0040-4039
出版者
Elsevier Ltd
其它主题
Moieties; Enol ethers; Steroid 17-oxime; Acid-labile group tolerance; Beckmann rearrangement; Nitriles; Ambient temperature; Regioselectivity; Perfluoroalkylsulfonyl fluoride; Quassin
语言
英语
类型
Journal Article; Text
2024-02-28
MODS
