Enantioselective Organocatalytic α-Fluorination of Cyclic Ketones

Kwiatkowski, Piotr; Beeson, T. D.; Conrad, Jay C.; MacMillan, David W. C.

doi:10.1021/ja111163u

Cited by 220 publications

(67 citation statements)

References 48 publications

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“…Subsequent hydrolysis of the iminium intermediate forms the chiral fluoroaldehyde and regenerates the organocatalyst. More recently, electrophilic, enantioselective fluorination of enol ethers, allyl silanes, oxindoles, and cyclic ketones were reported using cinchona alkaloids as a catalysts 88,89 . Nucleophilic, aliphatic fluorination by chiral organocatalysis has not yet been established, but transition-metal catalysis based on chiral palladium allyl complexes can be used to make allyl fluorides 90 enantioselectively 91 .…”

Section: Catalyzed Csp3–f and Csp3–cf3 Bond Formationmentioning

confidence: 99%

Catalysis for fluorination and trifluoromethylation

Furuya

Kamlet

Ritter

2011

Nature

1,980

623

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Preface Recent advances in catalysis have made the incorporation of fluorine into complex organic molecules easier than ever before, but selective, general, and practical fluorination reactions remain sought after. Fluorination of molecules often imparts desirable properties such as metabolic and thermal stability, and fluorinated molecules are therefore frequently used as pharmaceuticals or materials. Even with the latest advances in chemistry, carbon–fluorine bond formation in complex molecules is still a significant challenge. Within the last few years, new reactions to make organofluorides have emerged and exemplify how to overcome some of the intricate challenges associated with fluorination.

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Section: Catalyzed Csp3–f and Csp3–cf3 Bond Formationmentioning

confidence: 99%

Catalysis for fluorination and trifluoromethylation

Furuya

Kamlet

Ritter

2011

Nature

1,980

623

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“…7 However, α-fluorinated ketones are useful synthetic intermediates 8 and a direct route to these compounds would have significant value. Fluorine-substituted ketones are often prepared via electrophilic fluorinations and by other routes.…”

Section: Introductionmentioning

confidence: 99%

Fluoro-substituted ketones from nitriles using acidic and basic reaction conditions

Raja

Klumpp

2011

Tetrahedron Letters

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Fluoro-substituted aliphatic nitriles are shown to undergo the Houben-Hoesch reactions with arenes in CF3SO3H to give fluoro-substituted ketones in good yields. The fluorine substituents appear to enhance the reactivities of the nitriles (and the nitrilium ion intermediates) compared to similar aliphatic nitriles. Fluoro-substituted ketones are also shown to be accessible through the reactions of organometallic reagents and fluoro-substituted nitriles.

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“…Allo-Pregnanedione 69 an endogenous progestogen, has been fluorinated by the MacMillan group utilizing an enantioselective organocatalytic -fluorination reaction to give product 70. 33 After successfully investigating multiple cyclohexanone compounds, the MacMillan group utilized their findings to fluorinate a more complex cycloketone as seen in Scheme 23. Depending on which catalyst is used the selectivity of fluorination can be manipulated.…”

Section: 22mentioning

confidence: 99%

Selective fluorination of natural products

Luzzio¹,

Monsen²,

Zhdankin³

2017

Arkivoc

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Compounds derived from natural sources including animals, plants, and micro-organisms have been widely used for pharmaceuticals, materials, and agrochemicals. The use of these natural products has grown increasingly over the years and the demand for more improved, biologically active, and safer derivatives of natural products has been investigated by many researchers in the areas of synthetic and medicinal chemistry. Due to the unique characteristics of fluorinated compounds, and the increased or more favorable biological activity which usually accompanies fluorinated analogues of medicinally-important compounds, the fluorination of natural products has gained much attention. This review aims at exploring the range of specific natural product types that have been selectively fluorinated as well as how fluorination was expected to affect their biological activities and physiochemical properties.

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Enantioselective Organocatalytic α-Fluorination of Cyclic Ketones

Cited by 220 publications

References 48 publications

Catalysis for fluorination and trifluoromethylation

Catalysis for fluorination and trifluoromethylation

Fluoro-substituted ketones from nitriles using acidic and basic reaction conditions

Selective fluorination of natural products

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