Selective C-F bond cleavage

A versatile C4-building block, difluorinated Danishefsky s diene, was developed for the construction of fluorinated six-membered rings in the laboratory of K. Uneyama. The diene was prepared by the selective C-F bond cleavage of trifluoromethyl ketones. The reaction of this novel diene with benzaldehyde afforded the corresponding difluoro dihydropyrone in 92% ee in the presence of equimolar Ti(IV)-(R)-BINOL. ... 

Amii, H., Kobayashi, T., Hatamoto, Y. and Uneyama, K. (1999) Mg°-promoted selective C-F bond cleavage of trifluoromethyl ketones a convenient method for the synthesis of 2,2-difluoro enol silanes. J. Chem. Soc. Chem. Commun., 1323-1324... 

Silyl Enol Ethers. a,a-Difluorotrimethylsilyl enol ethers can be prepared through a Mg/TMSCl-promoted selective C-F bond cleavage of the corresponding trifluoromethyl ketones. An a,a-difluorinated analog of Danishefsky s diene was prepared in good... 

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See also in sourсe #XX -- [ ]

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