Efficient 1H NMR chiral discrimination of sulfoxides caused by the dynamic nature of (R,R)-3′,3″-biBINOL |
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| Authors: | Toshio Kawanami Kentaro Ishizuka Hiroshi Furuno Yoshihito Shiota Kazunari Yoshizawa Junji Inanaga |
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| Institution: | 1. Department of Molecular Chemistry, Graduate School of Sciences, Kyushu University, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan;2. Institute for Materials Chemistry and Engineering (IMCE), Kyushu University, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan;3. Green Asia Education Center, Kyushu University, 6-1 Kasuga-koen, Kasuga-city, Fukuoka 816-8580, Japan;4. Institute for Materials Chemistry and Engineering (IMCE), Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan |
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| Abstract: | A chiral BINOL dimer, (R,R)-3′,3″-BiBINOL, which possesses both rigid (atropos) and dynamic (tropos) axial chiralities, was found to work as an effective NMR chiral solvating reagent for the determination of the enantiomeric purities of various chiral sulfoxides. The unique chiral discrimination mechanism was also revealed by using DFT calculations and X-ray crystallographic analysis. |
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| Keywords: | Corresponding authors Tel /fax: +81 92 583 7902 |
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