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- W1969908028 startingPage "8588" @default.
- W1969908028 abstract "The polarity-mismatched perfluoroalkyl radical addition to electron-deficient alkenes was studied. For this study, several substrates having two polarity-different radical acceptors were employed to investigate the regiochemical courses of cascade reaction. In the case of substrate 1 having a methacryloyl moiety, we found polarity-mismatched perfluoroalkylation giving 15a–e as a major course over the polarity-matched perfluoroalkylation giving 16a–e. Moreover, in the case of substrates 2–7, perfluoroalkyl radicals selectively added to an electron-deficient alkene moiety of 2–7, to give polarity-mismatched perfluoroalkylation products without the formation of regioisomers. Next, the control of enantioselectivity was studied. In the case of substrates 1 and 3, the reaction proceeded with good enantioselectivities by employing a chiral Lewis acid, prepared from chiral box ligand 24 and Zn(OTf)2. For direct comparison, we also studied the reaction with other carbon radicals, derived from ICH2CO2Et, ICH2CN, BrC(CO2Et)2Me, and CCl3Br, which have electrophilic character." @default.
- W1969908028 created "2016-06-24" @default.
- W1969908028 creator A5010481180 @default.
- W1969908028 creator A5019675349 @default.
- W1969908028 creator A5037903237 @default.
- W1969908028 creator A5045623751 @default.
- W1969908028 creator A5061616865 @default.
- W1969908028 creator A5076437541 @default.
- W1969908028 date "2012-09-25" @default.
- W1969908028 modified "2023-10-18" @default.
- W1969908028 title "Polarity-Mismatched Addition of Electrophilic Carbon Radicals to an Electron-Deficient Acceptor: Cascade Radical Addition–Cyclization–Trapping Reaction" @default.
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