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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| Published in | Journal of the American Chemical Society Vol. 138; no. 42; pp. 13858 - 13861 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
26.10.2016
Amer Chemical Soc |
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| Online Access | Get full text |
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| 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. |
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| AbstractList | 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.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. 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. |
| Author | Jacobsen, Eric N Woerly, Eric M Banik, Steven M |
| AuthorAffiliation | Harvard University Department of Chemistry and Chemical Biology |
| AuthorAffiliation_xml | – name: Harvard University – name: Department of Chemistry and Chemical Biology |
| Author_xml | – sequence: 1 givenname: Eric M surname: Woerly fullname: Woerly, Eric M – sequence: 2 givenname: Steven M surname: Banik fullname: Banik, Steven M – sequence: 3 givenname: Eric N surname: Jacobsen fullname: Jacobsen, Eric N email: jacobsen@chemistry.harvard.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27709922$$D View this record in MEDLINE/PubMed |
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| Snippet | The enantioselective synthesis of 4-fluoroisochromanones via chiral aryl iodide-catalyzed fluorolactonization is reported. This methodology uses HF-pyridine as... The enantioselective synthesis of 4-fluoroisochromanones via chiral aryl iodide-catalyzed fluorolactonization is reported. This methodology uses HF•pyridine as... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary enantiomers fluorides lactones oxidants Physical Sciences Science & Technology standard operating procedures |
| Title | Enantioselective, Catalytic Fluorolactonization Reactions with a Nucleophilic Fluoride Source |
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