A simple protocol for NMR analysis of the enantiomeric purity of chiral hydroxylamines

D.A. Tickell; Mary F Mahon; S.D. Bull; T.D. James

doi:10.1021/ol303566k

A simple protocol for NMR analysis of the enantiomeric purity of chiral hydroxylamines

D.A. Tickell, Mary F Mahon, S.D. Bull, T.D. James

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

49 Citations (SciVal)

Abstract

A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral hydroxylamines by H NMR spectroscopic analysis is described, involving their treatment with 2-formylphenylboronic acid and enantiopure BINOL to afford a mixture of diastereomeric nitrono-boronate esters whose ratio is an accurate reflection of the enantiopurity of the parent hydroxylamine.

Original language	English
Pages (from-to)	860-863
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	4
DOIs	https://doi.org/10.1021/ol303566k
Publication status	Published - 15 Feb 2013

Access to Document

10.1021/ol303566k

Cite this

@article{44e3705a6cf0441bbcd3146be5b936cc,

title = "A simple protocol for NMR analysis of the enantiomeric purity of chiral hydroxylamines",

abstract = "A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral hydroxylamines by H NMR spectroscopic analysis is described, involving their treatment with 2-formylphenylboronic acid and enantiopure BINOL to afford a mixture of diastereomeric nitrono-boronate esters whose ratio is an accurate reflection of the enantiopurity of the parent hydroxylamine. ",

author = "D.A. Tickell and Mahon, \{Mary F\} and S.D. Bull and T.D. James",

year = "2013",

month = feb,

day = "15",

doi = "10.1021/ol303566k",

language = "English",

volume = "15",

pages = "860--863",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "4",

}

TY - JOUR

T1 - A simple protocol for NMR analysis of the enantiomeric purity of chiral hydroxylamines

AU - Tickell, D.A.

AU - Mahon, Mary F

AU - Bull, S.D.

AU - James, T.D.

PY - 2013/2/15

Y1 - 2013/2/15

N2 - A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral hydroxylamines by H NMR spectroscopic analysis is described, involving their treatment with 2-formylphenylboronic acid and enantiopure BINOL to afford a mixture of diastereomeric nitrono-boronate esters whose ratio is an accurate reflection of the enantiopurity of the parent hydroxylamine.

AB - A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral hydroxylamines by H NMR spectroscopic analysis is described, involving their treatment with 2-formylphenylboronic acid and enantiopure BINOL to afford a mixture of diastereomeric nitrono-boronate esters whose ratio is an accurate reflection of the enantiopurity of the parent hydroxylamine.

UR - https://www.scopus.com/pages/publications/84873964355

UR - http://dx.doi.org/10.1021/ol303566k

U2 - 10.1021/ol303566k

DO - 10.1021/ol303566k

M3 - Article

AN - SCOPUS:84873964355

SN - 1523-7060

VL - 15

SP - 860

EP - 863

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

A simple protocol for NMR analysis of the enantiomeric purity of chiral hydroxylamines

Abstract

Access to Document

Other files and links

Fingerprint

Cite this