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

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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.

Original languageEnglish
Pages (from-to)1587-1590
Number of pages4
JournalTetrahedron Asymmetry
Volume28
Issue number11
DOIs
Publication statusPublished - Nov 15 2017

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Sulfoxides
Chirality
chirality
Discrete Fourier transforms
Dimers
reagents
discrimination
purity
dimers
Nuclear magnetic resonance
X rays
nuclear magnetic resonance
x rays
naphthol BINOL

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

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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.",
author = "Toshio Kawanami and Kentaro Ishizuka and Hiroshi Furuno and Yoshihito Shiota and Kazunari Yoshizawa and Junji Inanaga",
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T1 - Efficient 1H NMR chiral discrimination of sulfoxides caused by the dynamic nature of (R,R)-3′,3″-biBINOL

AU - Kawanami, Toshio

AU - Ishizuka, Kentaro

AU - Furuno, Hiroshi

AU - Shiota, Yoshihito

AU - Yoshizawa, Kazunari

AU - Inanaga, Junji

PY - 2017/11/15

Y1 - 2017/11/15

N2 - 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.

AB - 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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