A simple chiral derivatisation protocol for H-1 NMR spectroscopic analysis of the enantiopurity of O-silyl-1,2-amino alcohols

Magdalena E Powell; Andrew M Kelly; Steven D Bull; Tony D James

doi:10.1016/j.tetlet.2008.12.013

A simple chiral derivatisation protocol for H-1 NMR spectroscopic analysis of the enantiopurity of O-silyl-1,2-amino alcohols

Magdalena E Powell, Andrew M Kelly, Steven D Bull, Tony D James

Department of Chemistry

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

29 Citations (SciVal)

Abstract

A simple chiral derivatisation protocol for determining the enantiopurity of O-silyl-protected-1,2-amino alcohols by H-1 NMR spectroscopic analysis is described, which involves their treatment with 2-formylphenylboronic acid and enantiopure (syn)-methyl-2,3-dihydroxy-3-phenylpropionate to afford mixtures of imino-boronate esters whose diastereoisomeric ratio is an accurate reflection of the enantiopurity of the parent amino alcohol.

Original language	English
Pages (from-to)	876-879
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2008.12.013
Publication status	Published - Feb 2009

Keywords

2-Amino alcohol
1
Chiral derivatisation agent
H-1 NMR spectroscopy
Enantiomeric excess
Boronate esters

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10.1016/j.tetlet.2008.12.013

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title = "A simple chiral derivatisation protocol for H-1 NMR spectroscopic analysis of the enantiopurity of O-silyl-1,2-amino alcohols",

abstract = "A simple chiral derivatisation protocol for determining the enantiopurity of O-silyl-protected-1,2-amino alcohols by H-1 NMR spectroscopic analysis is described, which involves their treatment with 2-formylphenylboronic acid and enantiopure (syn)-methyl-2,3-dihydroxy-3-phenylpropionate to afford mixtures of imino-boronate esters whose diastereoisomeric ratio is an accurate reflection of the enantiopurity of the parent amino alcohol.",

keywords = "2-Amino alcohol, 1, Chiral derivatisation agent, H-1 NMR spectroscopy, Enantiomeric excess, Boronate esters",

author = "Powell, \{Magdalena E\} and Kelly, \{Andrew M\} and Bull, \{Steven D\} and James, \{Tony D\}",

year = "2009",

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doi = "10.1016/j.tetlet.2008.12.013",

language = "English",

volume = "50",

pages = "876--879",

journal = "Tetrahedron Letters",

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T1 - A simple chiral derivatisation protocol for H-1 NMR spectroscopic analysis of the enantiopurity of O-silyl-1,2-amino alcohols

AU - Powell, Magdalena E

AU - Kelly, Andrew M

AU - Bull, Steven D

AU - James, Tony D

PY - 2009/2

Y1 - 2009/2

N2 - A simple chiral derivatisation protocol for determining the enantiopurity of O-silyl-protected-1,2-amino alcohols by H-1 NMR spectroscopic analysis is described, which involves their treatment with 2-formylphenylboronic acid and enantiopure (syn)-methyl-2,3-dihydroxy-3-phenylpropionate to afford mixtures of imino-boronate esters whose diastereoisomeric ratio is an accurate reflection of the enantiopurity of the parent amino alcohol.

AB - A simple chiral derivatisation protocol for determining the enantiopurity of O-silyl-protected-1,2-amino alcohols by H-1 NMR spectroscopic analysis is described, which involves their treatment with 2-formylphenylboronic acid and enantiopure (syn)-methyl-2,3-dihydroxy-3-phenylpropionate to afford mixtures of imino-boronate esters whose diastereoisomeric ratio is an accurate reflection of the enantiopurity of the parent amino alcohol.

KW - 2-Amino alcohol

KW - 1

KW - Chiral derivatisation agent

KW - H-1 NMR spectroscopy

KW - Enantiomeric excess

KW - Boronate esters

UR - https://www.scopus.com/pages/publications/58149334774

UR - http://dx.doi.org/10.1016/j.tetlet.2008.12.013

U2 - 10.1016/j.tetlet.2008.12.013

DO - 10.1016/j.tetlet.2008.12.013

M3 - Article

SN - 0040-4039

VL - 50

SP - 876

EP - 879

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

A simple chiral derivatisation protocol for H-1 NMR spectroscopic analysis of the enantiopurity of O-silyl-1,2-amino alcohols

Abstract

Keywords

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