Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 42, Pages 13858-13861Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b09499
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Funding
- NIH [GM043214]
- NSF
- Suzanne and Bob Wright postdoctoral fellowship from the Damon Runyon Cancer Research Foundation [DRG-2180-14]
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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.
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