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Asymmetric Fluorination of Cyclic Tetrasubstituted Alkenes with a Pendant Amide Groups under Dianionic Phase-Transfer Catalysis.
Niwa, Tomoki; Ujiie, Kiyoshi; Sato, Hitomi; Egami, Hiromichi; Hamashima, Yoshitaka.
Affiliation
  • Niwa T; School of Pharmaceutical Sciences, University of Shizuoka.
  • Ujiie K; School of Pharmaceutical Sciences, University of Shizuoka.
  • Sato H; School of Pharmaceutical Sciences, University of Shizuoka.
  • Egami H; School of Pharmaceutical Sciences, University of Shizuoka.
  • Hamashima Y; School of Pharmaceutical Sciences, University of Shizuoka.
Chem Pharm Bull (Tokyo) ; 66(10): 920-922, 2018.
Article in En | MEDLINE | ID: mdl-30270238
Asymmetric fluorination of cyclic tetrasubstituted alkenes with a pendant amide group was investigated under dianionic phase-transfer catalysis. Fluorination proceeded with high face selectivity, affording the corresponding allylic fluorides with a chiral tetrasubstituted carbon center with up to 97% enantiomeric excess (ee). It should be noted that deprotonative fluorination occurred mainly in preference to intramolecular nucleophilic attack of the amide group.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Cycloparaffins / Dicarboxylic Acids / Halogenation / Amides / Hydrocarbons, Fluorinated Language: En Journal: Chem Pharm Bull (Tokyo) Year: 2018 Type: Article

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Cycloparaffins / Dicarboxylic Acids / Halogenation / Amides / Hydrocarbons, Fluorinated Language: En Journal: Chem Pharm Bull (Tokyo) Year: 2018 Type: Article