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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.

SUBMITTER: Woerly EM

PROVIDER: S-EPMC5382122 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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Enantioselective, Catalytic Fluorolactonization Reactions with a Nucleophilic Fluoride Source.

Woerly Eric M EM Banik Steven M SM Jacobsen Eric N EN

Journal of the American Chemical Society 20161013 42

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 fluorinat ...[more]

PMID: 27709922

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