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

Q2 Chemistry

Tetrahedron, asymmetry Pub Date : 2017-11-15 DOI:10.1016/j.tetasy.2017.10.008

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

引用次数: 0

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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(R,R)-3′，3″-biBINOL动态性质引起的亚砜的高效1H NMR手性鉴别

一种手性二聚体(R,R)-3′，3″-BiBINOL具有刚性(对向)和动态(对向)的轴向手性，可作为一种有效的核磁共振手性溶剂化试剂，用于测定各种手性亚砜的对映体纯度。通过DFT计算和x射线晶体学分析，揭示了其独特的手性鉴别机理。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron, asymmetry 化学-无机化学与核化学

CiteScore

4.70

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： Cessation. Tetrahedron: Asymmetry presents experimental or theoretical research results of outstanding significance and timeliness on asymmetry in organic, inorganic, organometallic and physical chemistry, as well as its application to related disciplines, especially bio-organic chemistry. The journal publishes critical reviews, original research articles and preliminary communications dealing with all aspects of the chemical, physical and theoretical properties of non-racemic organic and inorganic materials and processes. Topics relevant to the journal include: the physico-chemical and biological properties of enantiomers; strategies and methodologies of asymmetric synthesis; resolution; chirality recognition and enhancement; analytical techniques for assessing enantiomeric purity and the unambiguous determination of absolute configuration; and molecular graphics and modelling methods for interpreting and predicting asymmetric phenomena. Papers describing the synthesis or properties of non-racemic molecules will be required to include a separate statement in the form of a Stereochemistry Abstract, for publication in the same issue, of the criteria used for the assignment of configuration and enantiomeric purity.