期刊
TETRAHEDRON LETTERS
卷 51, 期 45, 页码 5900-5903出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.08.090
关键词
Selectfluor; Allylic fluorination; Fluorohydroxylation
资金
- National Science Council of the Republic of China [NSC 99-2113-M-037-006-MY3]
- Kaohsiung Medical Research Foundation [KMU-Q099003]
A simple and straightforward synthesis of 1-substituted-4-aryl-5-fluoro-1,2,3,6-tetrahydropyridine (3) or 1-substituted 4-diarylmethanoyl-4-fluoropiperidine (6) by the treatment of piperidinyl exo- or endo-olefin with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate (Selectfluor) is reported. Two transformations from endo-olefin 1 to allylic fluoride 3 and from exo-olefin 2 to fluorohydrin 6 proceed via allylic fluorination and fluorohydroxylation in moderate yields. It presents two novel reactions promoted by Selectfluor and broadens the scope of application. (C) 2010 Elsevier Ltd. All rights reserved.
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