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Synthesis of α,α-Difluoro-β-amino Ketones from N -Boc-α-Amidosulfones and Pentafluoro- gem -diols.
Journal of Organic Chemistry 2024 April 13
To circumvent the synthesis and isolation of imines, a method was devised to construct α,α-difluoro-β-amino ketones from N -Boc-α-amidosulfones. The reactive nucleophiles, difluoroenolates, are generated in situ from the pentafluoro- gem -diols using cesium fluoride in pyridine. NMR studies confirm the role of the α-amidosulfones in this process. Incubation of the α,α-difluoro-β-amino ketones in rat serum demonstrates the relative stability of this structure as well as its value as a chemical probe or lead.
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