Kargbo, Robert published the artcileReadily Accessible, Modular, and Tuneable BINOL 3,3′-Perfluoroalkylsulfones: Highly Efficient Catalysts for Enantioselective In-Mediated Imine Allylation, SDS of cas: 126613-06-7, the publication is Journal of the American Chemical Society (2007), 129(13), 3846-3847, database is CAplus and MEDLINE.
Thia-Fries rearrangement of BINOL perfluoroalkylsulfonates affords readily derivatized novel perfluoroalkyl mono- and disulfone BINOL ligands in just two steps from enantiomerically pure BINOL. These electron-demanding BINOLs were successfully applied as catalysts for indium-mediated allylation of N-acylhydrazones. A general and highly enantioselective catalytic process is described, in which the presence of two perfluoroalkylsulfone (SO2RF, RF = CF3, n-C4F9, n-C8F17) groups is crucial for activity and selectivity. The allylation process affords the corresponding homoallylic amines in up to 99% yield and 99% ee. E.g., allylation of 3-{2-ClC6H4CH:N}oxazol (oxazol = 2-oxazolidinonyl) with allyl bromide in the presence of indium and (R)-3,3′-bis(trifluoromethanesulfonyl)-2,2′-dihydroxy-1,1′-binaphthalene gave 3-{2-ClC6H4(H2C:CHCH2)CHNH}oxazol in 99% yield and 99% ee.
Journal of the American Chemical Society published new progress about 126613-06-7. 126613-06-7 belongs to esters-buliding-blocks, auxiliary class Chiral Diphenols, name is (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), and the molecular formula is C22H12F6O6S2, SDS of cas: 126613-06-7.
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