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Tetrakis(dimethylamino)ethylene (TDAE) as a useful reductant of some chlorodifluoromethylated ketones. A new approach for the synthesis of α,α-difluoroketone derivatives

Tetrakis(dimethylamino)ethylene (TDAE) was found to be an effective reductant of chlorodifluoromethylated ketones 1–3. The generated α,α-difluoroacetyl anion was trapped with several aldehydes 4–7, under mild conditions, to give the corresponding 2,2-difluoro-3-hydroxy ketone derivatives 8–13, in mo...

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Bibliographic Details
Published in:Tetrahedron letters 1998-11, Vol.39 (48), p.8853-8856
Main Authors: Burkholder, Conrad, Dolbier, William R., Me´debielle, Maurice, Ndedi, Alexandre
Format: Article
Language:English
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Summary:Tetrakis(dimethylamino)ethylene (TDAE) was found to be an effective reductant of chlorodifluoromethylated ketones 1–3. The generated α,α-difluoroacetyl anion was trapped with several aldehydes 4–7, under mild conditions, to give the corresponding 2,2-difluoro-3-hydroxy ketone derivatives 8–13, in moderate yields. Tetrakis(dimethylamino)ethylene (TDAE) was found to be an effective reductant of chlorodifluoromethyl ketones 1–3. The generated α,α-difluoroacetyl anion was trapped with several aldehydes 4–7, under mild conditions, to give the corresponding 2,2-difluoro-3-hydroxy ketone derivatives 8–13, in moderate yields. [Display omitted]
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)02028-0