title: Diastereoselective Synthesis of Fluorine-Containing Pyrrolizidines via Triphenylcarbenium Tetrafluoroborate-Promoted Carbofluorination of N-3-Arylpropargylpyrrolidine-Tethered Tertiary Allylic Alcohols.
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.
authors.affiliation: Department of Chemistry, National Taiwan Normal University , 88 Ding-Jou Road, Section 4, Taipei 11677, Taiwan, Republic of China.
authors.forename: Ming-Chang P
authors.initials: MC
authors.lastname: Yeh
authors.affiliation: Department of Chemistry, National Taiwan Normal University , 88 Ding-Jou Road, Section 4, Taipei 11677, Taiwan, Republic of China.
authors.forename: Hsiao-Feng
authors.initials: HF
authors.lastname: Chen
authors.affiliation: Department of Chemistry, National Taiwan Normal University , 88 Ding-Jou Road, Section 4, Taipei 11677, Taiwan, Republic of China.
authors.forename: Yu-Ya
authors.initials: YY
authors.lastname: Huang
authors.affiliation: Department of Chemistry, National Taiwan Normal University , 88 Ding-Jou Road, Section 4, Taipei 11677, Taiwan, Republic of China.
authors.forename: Yu-Ting
authors.initials: YT
authors.lastname: Weng