ArticleThe Journal of organic chemistry2018
Magnesium-Promoted Additions of Difluoroenolates to Unactivated Imines.
Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Advances in the Different Synthetic Routes of Fluorinated Hydrazines.Chemical record (New York, N.Y.) · 2026Review
- Stability studies of β-Amino- and β-Hydroxy difluoromethyl ketones in rat serum and rat liver microsomes.Bioorganic & medicinal chemistry letters · 2024Article
- Synthesis of α,α-Difluoro-β-amino Ketones fromThe Journal of organic chemistry · 2024Article
- Transient Formation of Hemiketals from Pentafluoro-Journal of fluorine chemistry · 2023Article
- Recent progress in the chemistry of β-aminoketones.RSC advances · 2022Review
- Generation of formaldehyde and formaldehyde-dChemical communications (Cambridge, England) · 2022Article
- Synthesis of Difluorinated Halohydrins by the Chemoselective Addition of Difluoroenolates to α-Haloketones.Organic letters · 2021Article
- Controlling the Cleavage of Carbon-Carbon Bonds To Generate α,α-Difluorobenzyl Carbanions for the Construction of Difluoromethylbenzenes.The Journal of organic chemistry · 2019Article
- Agonists of the γ-aminobutyric acid type B (GABABioorganic & medicinal chemistry letters · 2018Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
Although there are many synthetic methods to produce fluorinated and trifluoromethylated organic structures, the construction of difluoromethylated compounds remains a synthetic challenge. We have discovered that unactivated imines will react with difluoroenolates under exceedingly mild conditions when using magnesium salts and organic bases. We have applied this approach to the iminoaldol reaction to produce difluoromethylene groups as α,α-difluoro-β-amino-carbonyl groups. This method provides synthetically useful quantities of difficult to access α,α-difluoro-β-aminoketones without the need of protecting groups or the use of activated imines. Moreover, we have applied this strategy to create analogues of the dual orexin receptor antagonist, almorexant, in only two synthetic steps.
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