Literature DB >> 16671759

Simple protocol for NMR analysis of the enantiomeric purity of diols.

Andrew M Kelly1, Yolanda Pérez-Fuertes, Susumu Arimori, Steven D Bull, Tony D James.   

Abstract

[reaction: see text] A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral 1,2-, 1,3-, and 1,4-diols by (1)H NMR spectroscopic analysis is described. The method involves treatment with 2-formylphenylboronic acid and enantiopure alpha-methylbenzylamine to afford a mixture of diastereoisomeric iminoboronate esters whose ratio is an accurate reflection of the enantiopurity of the parent diol.

Entities:  

Year:  2006        PMID： 16671759     DOI： 10.1021/ol0602351

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  The Bull-James assembly as a chiral auxiliary and shift reagent in kinetic resolution of alkyne amines by the CuAAC reaction.

Authors:  William D G Brittain; Brette M Chapin; Wenlei Zhai; Vincent M Lynch; Benjamin R Buckley; Eric V Anslyn; John S Fossey
Journal:  Org Biomol Chem       Date:  2016-11-22       Impact factor: 3.876

2.  Pattern-based recognition for the rapid determination of identity, concentration, and enantiomeric excess of subtly different threo diols.

Authors:  Shagufta H Shabbir; Leo A Joyce; Gabriella M da Cruz; Vincent M Lynch; Steven Sorey; Eric V Anslyn
Journal:  J Am Chem Soc       Date:  2009-09-16       Impact factor: 15.419

3.  Molecular recognition and self-assembly special feature: A general protocol for creating high-throughput screening assays for reaction yield and enantiomeric excess applied to hydrobenzoin.

Authors:  Shagufta H Shabbir; Clinton J Regan; Eric V Anslyn
Journal:  Proc Natl Acad Sci U S A       Date:  2009-03-30       Impact factor: 11.205

Review 4.  Self and directed assembly: people and molecules.

Authors:  Tony D James
Journal:  Beilstein J Org Chem       Date:  2016-03-01       Impact factor: 2.883

5.  Post-Assembly Reactivity of N-Aryl Iminoboronates: Reversible Radical Coupling and Unusual B-N Dynamic Covalent Chemistry.

Authors:  Evan N Keyzer; Alexandru Sava; Tanya K Ronson; Jonathan R Nitschke; Anna J McConnell
Journal:  Chemistry       Date:  2018-07-25       Impact factor: 5.236

6.  NMR analysis of the enantiomeric purity of chiral diols by a new chiral boron agent.

Authors:  Xuebo Zhang; Jing Xu; Zhaofeng Sun; Guangling Bian; Ling Song
Journal:  RSC Adv       Date:  2022-02-08       Impact factor: 3.361

7.  A colour-tunable chiral AIEgen: reversible coordination, enantiomer discrimination and morphology visualization.

Authors:  Jesse Roose; Anakin Chun Sing Leung; Jia Wang; Qian Peng; Herman H-Y Sung; Ian Duncan Williams; Ben Zhong Tang
Journal:  Chem Sci       Date:  2016-06-02       Impact factor: 9.825

Review 8.  New Advances in the Synthetic Application of Enantiomeric 1-Phenylethylamine (α-PEA): Privileged Chiral Inducer and Auxiliary.

Authors:  Marzena Wosińska-Hrydczuk; Jacek Skarżewski
Journal:  Molecules       Date:  2020-10-23       Impact factor: 4.411
  8 in total

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