ja6b09499_si_001.pdf (5.17 MB)
Enantioselective, Catalytic Fluorolactonization Reactions with a Nucleophilic Fluoride Source
journal contribution
posted on 2016-10-06, 00:00 authored by Eric M. Woerly, Steven M. Banik, Eric N. JacobsenThe 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.
History
Usage metrics
Categories
Keywords
EnantioselectivediastereoselectivityNucleophilic Fluoride Sourcelactonization reactionsHF-pyridineregioselectivitychiral aryl iodide-catalyzed fluorolactonizationaccessmethodologylactone4- fluoroisochromanoneselectrophilic fluorination protocolsfluorine-bearing stereogenic centersenantioselective synthesisperacid stoichiometric oxidantnucleophilic fluoride sourceCatalytic Fluorolactonization Reactions
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC