Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR

Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR

In this article, we demonstrate that (S)-3-phenyl-2-(selenophenyl)propan-1-ol can be successfully employed as chiral derivatizing agent for enantiomeric excess determination of chiral carboxylic acid substrates via 77Se NMR. The required derivatives are obtained by mixing the chiral derivatizing agent with the non racemic carboxylic acid substrate directly in the NMR tube and determining the enantiomeric excess with just one spectrum. The best results were obtained with (S)-3-phenyl-2- (selenophenyl)propan-1-ol, which showed good anysochronies of the selenium signals, ranging from Δδ = 22 Hz to Δδ = 211 Hz, even with the stereocenter and the selenium atom five bonds apart.

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Main Authors: Ferreira,Jeiely G, Gonçalves,Simone M. C
Format: Digital revista
Language:English
Published: Sociedade Brasileira de Química 2010
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010001100002
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spelling oai:scielo:S0103-505320100011000022010-12-15Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMRFerreira,Jeiely GGonçalves,Simone M. C enantiomeric excess derivatizing agent selenium NMR chiral non racemic substrates In this article, we demonstrate that (S)-3-phenyl-2-(selenophenyl)propan-1-ol can be successfully employed as chiral derivatizing agent for enantiomeric excess determination of chiral carboxylic acid substrates via 77Se NMR. The required derivatives are obtained by mixing the chiral derivatizing agent with the non racemic carboxylic acid substrate directly in the NMR tube and determining the enantiomeric excess with just one spectrum. The best results were obtained with (S)-3-phenyl-2- (selenophenyl)propan-1-ol, which showed good anysochronies of the selenium signals, ranging from Δδ = 22 Hz to Δδ = 211 Hz, even with the stereocenter and the selenium atom five bonds apart.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.21 n.11 20102010-01-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010001100002en10.1590/S0103-50532010001100002
institution SCIELO
collection OJS
country Brasil
countrycode BR
component Revista
access En linea
databasecode rev-scielo-br
tag revista
region America del Sur
libraryname SciELO
language English
format Digital
author Ferreira,Jeiely G
Gonçalves,Simone M. C
spellingShingle Ferreira,Jeiely G
Gonçalves,Simone M. C
Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR
author_facet Ferreira,Jeiely G
Gonçalves,Simone M. C
author_sort Ferreira,Jeiely G
title Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR
title_short Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR
title_full Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR
title_fullStr Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR
title_full_unstemmed Enantiomeric excess detection with (S)-3-Phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77Se NMR
title_sort enantiomeric excess detection with (s)-3-phenyl-2-(selenophenyl)propan-1-ol derivatizing agent via mix and shake 77se nmr
description In this article, we demonstrate that (S)-3-phenyl-2-(selenophenyl)propan-1-ol can be successfully employed as chiral derivatizing agent for enantiomeric excess determination of chiral carboxylic acid substrates via 77Se NMR. The required derivatives are obtained by mixing the chiral derivatizing agent with the non racemic carboxylic acid substrate directly in the NMR tube and determining the enantiomeric excess with just one spectrum. The best results were obtained with (S)-3-phenyl-2- (selenophenyl)propan-1-ol, which showed good anysochronies of the selenium signals, ranging from Δδ = 22 Hz to Δδ = 211 Hz, even with the stereocenter and the selenium atom five bonds apart.
publisher Sociedade Brasileira de Química
publishDate 2010
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010001100002
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AT goncalvessimonemc enantiomericexcessdetectionwiths3phenyl2selenophenylpropan1olderivatizingagentviamixandshake77senmr
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