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

doi:10.1016/j.tetasy.2017.10.008

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

Department of Fundamental Organic Chemistry

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

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 language	English
Pages (from-to)	1587-1590
Number of pages	4
Journal	Tetrahedron Asymmetry
Volume	28
Issue number	11
DOIs	https://doi.org/10.1016/j.tetasy.2017.10.008
Publication status	Published - Nov 15 2017

All Science Journal Classification (ASJC) codes

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/j.tetasy.2017.10.008

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

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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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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UR - https://www.scopus.com/pages/publications/85032890513#tab=citedBy

U2 - 10.1016/j.tetasy.2017.10.008

DO - 10.1016/j.tetasy.2017.10.008

M3 - Article

AN - SCOPUS:85032890513

SN - 0957-4166

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JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 11

ER -

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

Abstract

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