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

Toshio Kawanami, Kentaro Ishizuka, Hiroshi Furuno, Yoshihito Shiota, Kazunari Yoshizawa, Junji Inanaga

Research output: Contribution to journalArticlepeer-review

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

All Science Journal Classification (ASJC) codes

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

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