Efficient 1H NMR chiral discrimination of sulfoxides caused by the dynamic nature of (R,R)-3′,3″-biBINOL

[Display omitted] 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...

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Published inTetrahedron: asymmetry Vol. 28; no. 11; pp. 1587 - 1590
Main Authors Kawanami, Toshio, Ishizuka, Kentaro, Furuno, Hiroshi, Shiota, Yoshihito, Yoshizawa, Kazunari, Inanaga, Junji
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 01.11.2017
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Summary:[Display omitted] 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.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2017.10.008