title: Enantioselective, Catalytic Fluorolactonization Reactions with a Nucleophilic Fluoride Source.
abstract: 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 centers in high enantio- and diastereoselectivity. The regioselectivity observed in these lactonization reactions is complementary to that obtained with established asymmetric electrophilic fluorination protocols.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
authors.forename: Eric M
authors.initials: EM
authors.lastname: Woerly
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
authors.forename: Steven M
authors.initials: SM
authors.lastname: Banik
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
authors.forename: Eric N
authors.initials: EN
authors.lastname: Jacobsen