Diastereoselective Synthesis of Fluorine-Containing Pyrrolizidines via Triphenylcarbenium Tetrafluoroborate-Promoted Carbofluorination of N-3-Arylpropargylpyrrolidine-Tethered Tertiary Allylic Alcohol
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- 作者：Ming-Chang P. Yeh ; Hsiao-Feng Chen ; Yu-Ya Huang ; Yu-Ting Weng
- 刊名：Journal of Organic Chemistry
- 出版年：2015
- 出版时间：November 6, 2015
- 年：2015
- 卷：80
- 期：21
- 页码：10892-10903
- 全文大小：475K
- ISSN：1520-6904
文摘
Inexpensive and air stable triphenylcarbenium tetrafluoroborate efficiently promoted the carbofluorination of N-arylpropargylpyrrolidines bearing a tertiary allylic alcohol tether at the 2-position of the pyrrolidine ring to provide 1-isobutenyl-2-(fluoro(phenyl)methylenylhexahydro-1H-pyrrolizidines in a stereoselective fashion. When subjected to bis(trifluoromethane)sulfonamide, the same substrates underwent cycloisomerization reaction within minutes to generate 1-isobutenyl-2-benzoylhexahydro-1H-pyrrolizidines with excellent stereoselectivity.