Enantioselective, Catalytic Fluorolactonization Reactions with a Nucleophilic Fluoride Source

• Published in: Journal of the American Chemical Society Vol. 138; no. 42; pp. 13858 - 13861
• Main Authors: Woerly, Eric M, Banik, Steven M, Jacobsen, Eric N
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 26.10.2016; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; enantiomers; fluorides; lactones; oxidants; Physical Sciences; Science & Technology; standard operating procedures; ALKENES; REAGENTS; AMINOFLUORINATION; ELECTROPHILIC FLUOROCYCLIZATION; ALPHA-FLUORINATION; CARBOXYLIC-ACIDS; DIFLUORINATION

The enantioselective synthesis of 4-fluoroisochromanones via chiral aryl iodide-catalyzed fluorolactonization is reported. This methodology uses HF-pyridine as a nucleophilic fluoride source with a peracid stoichiometric oxidant and provides access to lactones containing fluorine-bearing stereogenic...