Diastereoselective Synthesis of Fluorine-Containing Pyrrolizidines via Triphenylcarbenium Tetrafluoroborate-Promoted Carbofluorination of N-3-Arylpropargylpyrrolidine-Tethered Tertiary Allylic Alcohols

Ming-Chang P. Yeh, Hsiao Feng Chen, Yu Ya Huang, Yu Ting Weng

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)10892-10903
Number of pages12
JournalJournal of Organic Chemistry
Volume80
Issue number21
DOIs
Publication statusPublished - 2015 Nov 6

ASJC Scopus subject areas

  • Organic Chemistry

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