Asymmetric Fluorofunctionalizations with Carboxylate‐Based Phase‐Transfer Catalysts
Fluorine is an attractive element in the field of pharmaceutical and agrochemical chemistry due to its unique properties. Considering the chiral environment in nature, where enantiomers often show different biological activities, the introduction of fluorine atom(s) into organic molecules to make ch...
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| Published in | Chemical record Vol. 23; no. 7; pp. e202200285 - n/a |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
United States
Wiley Subscription Services, Inc
01.07.2023
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| Abstract | Fluorine is an attractive element in the field of pharmaceutical and agrochemical chemistry due to its unique properties. Considering the chiral environment in nature, where enantiomers often show different biological activities, the introduction of fluorine atom(s) into organic molecules to make chiral fluorinated compounds is an important subject. Herein, we describe the story of the development of our chiral carboxylate‐based phase‐transfer catalysts and their applications for asymmetric fluorocyclizations of alkenes bearing a carboxylic acid, an amide, and an oxime as an internal nucleophile with a dicationic fluorinating reagent, Selectfluor. We also describe dearomative fluorinations of indole derivatives, 2‐naphthols, and resorcinols.
This personal account describes the design and synthesis of novel carboxylate‐based phase‐transfer catalysts for fluorination with Selectfluor. The catalysts enable various enantioselective fluorofunctionalizations of alkene derivatives and (hetero)aromatic compounds. The advantages of our catalytic system, its synthetic utility, and detailed mechanistic studies uncovering a unique catalytic cycle are also discussed briefly. |
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| AbstractList | Fluorine is an attractive element in the field of pharmaceutical and agrochemical chemistry due to its unique properties. Considering the chiral environment in nature, where enantiomers often show different biological activities, the introduction of fluorine atom(s) into organic molecules to make chiral fluorinated compounds is an important subject. Herein, we describe the story of the development of our chiral carboxylate‐based phase‐transfer catalysts and their applications for asymmetric fluorocyclizations of alkenes bearing a carboxylic acid, an amide, and an oxime as an internal nucleophile with a dicationic fluorinating reagent, Selectfluor. We also describe dearomative fluorinations of indole derivatives, 2‐naphthols, and resorcinols. Fluorine is an attractive element in the field of pharmaceutical and agrochemical chemistry due to its unique properties. Considering the chiral environment in nature, where enantiomers often show different biological activities, the introduction of fluorine atom(s) into organic molecules to make chiral fluorinated compounds is an important subject. Herein, we describe the story of the development of our chiral carboxylate-based phase-transfer catalysts and their applications for asymmetric fluorocyclizations of alkenes bearing a carboxylic acid, an amide, and an oxime as an internal nucleophile with a dicationic fluorinating reagent, Selectfluor. We also describe dearomative fluorinations of indole derivatives, 2-naphthols, and resorcinols.Fluorine is an attractive element in the field of pharmaceutical and agrochemical chemistry due to its unique properties. Considering the chiral environment in nature, where enantiomers often show different biological activities, the introduction of fluorine atom(s) into organic molecules to make chiral fluorinated compounds is an important subject. Herein, we describe the story of the development of our chiral carboxylate-based phase-transfer catalysts and their applications for asymmetric fluorocyclizations of alkenes bearing a carboxylic acid, an amide, and an oxime as an internal nucleophile with a dicationic fluorinating reagent, Selectfluor. We also describe dearomative fluorinations of indole derivatives, 2-naphthols, and resorcinols. Fluorine is an attractive element in the field of pharmaceutical and agrochemical chemistry due to its unique properties. Considering the chiral environment in nature, where enantiomers often show different biological activities, the introduction of fluorine atom(s) into organic molecules to make chiral fluorinated compounds is an important subject. Herein, we describe the story of the development of our chiral carboxylate‐based phase‐transfer catalysts and their applications for asymmetric fluorocyclizations of alkenes bearing a carboxylic acid, an amide, and an oxime as an internal nucleophile with a dicationic fluorinating reagent, Selectfluor. We also describe dearomative fluorinations of indole derivatives, 2‐naphthols, and resorcinols. This personal account describes the design and synthesis of novel carboxylate‐based phase‐transfer catalysts for fluorination with Selectfluor. The catalysts enable various enantioselective fluorofunctionalizations of alkene derivatives and (hetero)aromatic compounds. The advantages of our catalytic system, its synthetic utility, and detailed mechanistic studies uncovering a unique catalytic cycle are also discussed briefly. |
| Author | Egami, Hiromichi Hamashima, Yoshitaka |
| Author_xml | – sequence: 1 givenname: Hiromichi surname: Egami fullname: Egami, Hiromichi organization: University of Shizuoka 52-1 Yada, Suruga-ku – sequence: 2 givenname: Yoshitaka surname: Hamashima fullname: Hamashima, Yoshitaka email: hamashima@u-shizuoka-ken.ac.jp organization: University of Shizuoka 52-1 Yada, Suruga-ku |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/36734199$$D View this record in MEDLINE/PubMed |
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| Keywords | fluorination difunctionalization asymmetric reaction phase-transfer catalyst dearomatization |
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| Snippet | Fluorine is an attractive element in the field of pharmaceutical and agrochemical chemistry due to its unique properties. Considering the chiral environment in... |
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| SubjectTerms | Agrochemicals Alkenes asymmetric reaction Asymmetry Carboxylic acids Catalysts dearomatization difunctionalization Enantiomers Fluorination Fluorine Indoles Nucleophiles Organic chemistry Phase transfer catalysts phase-transfer catalyst Reagents |
| Title | Asymmetric Fluorofunctionalizations with Carboxylate‐Based Phase‐Transfer Catalysts |
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