Yang Ming-Hsiu, Orsi Douglas L, Altman Ryan A
Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045 (USA).
Angew Chem Int Ed Engl. 2015 Feb 16;54(8):2361-5. doi: 10.1002/anie.201410039. Epub 2015 Jan 7.
α,α-Difluoroketones possess unique physicochemical properties that are useful for developing therapeutics and probes for chemical biology. To access the α-allyl-α,α-difluoroketone substructure, complementary palladium-catalyzed decarboxylative allylation reactions were developed to provide linear and branched α-allyl-α,α-difluoroketones. For these orthogonal processes, the fluorination pattern of the substrate enabled the ligands to dictate the regioselectivity of the transformations.
α,α-二氟酮具有独特的物理化学性质,这对于开发治疗药物和化学生物学探针很有用。为了获得α-烯丙基-α,α-二氟酮亚结构,人们开发了互补的钯催化脱羧烯丙基化反应,以提供直链和支链的α-烯丙基-α,α-二氟酮。对于这些正交反应,底物的氟化模式使配体能够决定转化反应的区域选择性。