Enantioselective, Catalytic Fluorolactonization Reactions with a Nucleophilic Fluoride Source

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...

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Bibliographic Details
Published inJournal 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
LanguageEnglish
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
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Summary: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.
Bibliography:NIH RePORTER
ObjectType-Article-1
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content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.6b09499