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- W2064030448 abstract "Two new C2-symmetric benzoimidazolium tetrafluoroborates 19 and 20 were prepared from (1S)-(+)-camphorquinone 1 in seven and eight steps, respectively. Thus, N1-((1S,2R,3S,4R)-1,7,7-trimethyl-4′-methylenedihydro-3′H-spiro[bicyclo[2.2.1]heptane-2,2′-furan]-3-yl)benzene-1,2-diamine 11, available in three steps from 1, was first condensed with 1 to afford amino imines 12 and 13/13′. [3 + 2] Cycloaddition of trimethylenemethane (TMM) to 12 or 13/13′ gave cycloadduct 17, which was successfully reduced to diamine 4 using NaCNBH3. Catalytic hydrogenation of methylene groups of 4 gave the methyl analogue 18. Finally, cyclization of diamines 4 and 18 with triethyl orthoformate furnished the desired C2-symmetric benzoimidazolium tetrafluoroborates 19 and 20, respectively. The structures were determined by NMR techniques, NOESY spectroscopy, and X-ray diffraction." @default.
- W2064030448 created "2016-06-24" @default.
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- W2064030448 date "2008-02-01" @default.
- W2064030448 modified "2023-09-27" @default.
- W2064030448 title "Synthesis of novel C2-symmetric 1,3-bis{(1S,2R,3S,4R)-1,7,7-trimethyl-3′H-spiro[bicyclo[2.2.1]heptane-2,2′-furan]-3-yl}benzoimidazolium tetrafluoroborates" @default.
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- W2064030448 doi "https://doi.org/10.1016/j.tetasy.2008.01.005" @default.
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