Simple protocol for NMR analysis of the enantiomeric purity of diols

A M Kelly; Y Perez-Fuertes; S Arimori; S D Bull; T D James

doi:10.1021/ol0602351

Simple protocol for NMR analysis of the enantiomeric purity of diols

A M Kelly, Y Perez-Fuertes, S Arimori, S D Bull, T D James

Department of Chemistry

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

65 Citations (Scopus)

Abstract

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

Original language	English
Pages (from-to)	1971-1974
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	10
DOIs	https://doi.org/10.1021/ol0602351
Publication status	Published - 2006

Access to Document

10.1021/ol0602351

Fingerprint Dive into the research topics of 'Simple protocol for NMR analysis of the enantiomeric purity of diols'. Together they form a unique fingerprint.

Cite this

@article{7c937a4d19d94ba7b9d7836bf0729613,

title = "Simple protocol for NMR analysis of the enantiomeric purity of diols",

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

author = "Kelly, {A M} and Y Perez-Fuertes and S Arimori and Bull, {S D} and James, {T D}",

note = "ID number: ISI:000237420200003",

year = "2006",

doi = "10.1021/ol0602351",

language = "English",

volume = "8",

pages = "1971--1974",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "10",

}

TY - JOUR

T1 - Simple protocol for NMR analysis of the enantiomeric purity of diols

AU - Kelly, A M

AU - Perez-Fuertes, Y

AU - Arimori, S

AU - Bull, S D

AU - James, T D

N1 - ID number: ISI:000237420200003

PY - 2006

Y1 - 2006

N2 - A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral 1,2-, 1,3-, and 1,4-diols by H-1 NMR spectroscopic analysis is described. The method involves treatment with 2-formylphenylboronic acid and enantiopure alpha-methylbenzylamine to afford a mixture of diastereolsomeric iminoboronate esters whose ratio is an accurate reflection of the enantiopurity of the parent diol.

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

U2 - 10.1021/ol0602351

DO - 10.1021/ol0602351

M3 - Article

VL - 8

SP - 1971

EP - 1974

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 10

ER -