SYNTHESIS OF Α-Fluoro ALDEHYDES AND KETONES. A REVIEW

Davis, Franklin A.; Kasu, P. V. N.

doi:10.1080/00304949909355704

Cited by 44 publications

(11 citation statements)

References 37 publications

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“…The one asymmetric synthesis of 3-fluorophenylalanine, where Schollkopf's bis lactim ether strategy was employed, resulted in low overall yields and mixtures of products , and in the sulfinimine ( N -sulfinyl imine)-mediated asymmetric Strecker synthesis prompted studies aimed at the development of a general protocol for the asymmetric synthesis of β-fluoro α-amino acids. …”

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confidence: 99%

Efficient Asymmetric Synthesis of β-Fluoro α-Amino Acids

1999

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confidence: 99%

Efficient Asymmetric Synthesis of β-Fluoro α-Amino Acids

1999

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“…27 Monofluorination procedures for regular ketones at their α-carbon are known. [28][29][30] However, a reaction of alkynone 3a with NFSI (1 equiv), in the presence of the inorganic base ( potassium carbonate), leads to isolation of the difluoro derivative 4a. 31 Since monofluorination of regular ketones can also be accomplished under organocatalytic conditions, 32 an analogous approach was investigated.…”

Section: Resultsmentioning

confidence: 99%

Room temperature syntheses of entirely diverse substituted β-fluorofurans

Wheeler

Dembiński

2012

Org. Biomol. Chem.

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Synthesis of highly substituted 3-fluorofurans is reported. The sequence began with preparation of tert-butyldimethylsilyl alk-1-en-3-yn-1-yl ethers from 1,4-disubstituted alk-3-yn-1-ones. Subsequent fluorination of alkenynyl silyl ethers with Selectfluor gave 2-fluoroalk-3-yn-1-ones in almost quantitative yield. Subsequent 5-endo-dig cyclizations using chlorotriphenylphosphine gold(I)/silver trifluoromethanesulfonate (5/5 mol%), N-bromo- or N-iodosuccinimide and gold(I) chloride/zinc bromide (5/20 mol%), all at room temperature, provided a facile method for the generation of substituted 3-fluoro-, 3-bromo-4-fluoro-, and 3-fluoro-4-iodofurans in good yields. Also, 2,2-difluoroalk-3-yn-1-ones were prepared by fluorination of alk-3-yn-1-ones under organocatalytic conditions. The structures of (Z)-tert-butyldimethylsilyl but-1-en-3-yn-1-yl ether, 3-bromo-4-fluorofuran, and 3-fluoro-4-(phenylethynyl)furan were confirmed by X-ray crystallography.

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“…Several stereoselective methods are used for synthesis of optically active molecules bearing a CaF bond at the stereogenic carbon atom [72,73]. Several stereoselective methods are used for synthesis of optically active molecules bearing a CaF bond at the stereogenic carbon atom [72,73].…”

Section: Fluorination Reactionsmentioning

confidence: 99%