Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone

Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone

The synthesis of a series of chiral secondary alcohols derived from (R)-carvone, and the stereochemical outcome of their reaction with (±)-ibuprofen, is reported. The racemic drug was transformed into the corresponding diastereomeric esters mediated by DCC/DMAP, affording up to 5.7:1 diastereomeric ratios of the esters derived from either (S)- or (R)-ibuprofen, depending on the type of chiral auxiliary employed.

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Bibliographic Details
Main Authors: Amongero,Marcela, Visnovezky,Damian, Kaufman,Teodoro S.
Format: Digital revista
Language:English
Published: Sociedade Brasileira de Química 2010
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000600011
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spelling oai:scielo:S0103-505320100006000112010-07-19Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvoneAmongero,MarcelaVisnovezky,DamianKaufman,Teodoro S. ibuprofen carvone Steglich esterification chiral auxiliaries chiral secondary alcohols The synthesis of a series of chiral secondary alcohols derived from (R)-carvone, and the stereochemical outcome of their reaction with (±)-ibuprofen, is reported. The racemic drug was transformed into the corresponding diastereomeric esters mediated by DCC/DMAP, affording up to 5.7:1 diastereomeric ratios of the esters derived from either (S)- or (R)-ibuprofen, depending on the type of chiral auxiliary employed.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.21 n.6 20102010-01-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000600011en10.1590/S0103-50532010000600011
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 Amongero,Marcela
Visnovezky,Damian
Kaufman,Teodoro S.
spellingShingle Amongero,Marcela
Visnovezky,Damian
Kaufman,Teodoro S.
Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone
author_facet Amongero,Marcela
Visnovezky,Damian
Kaufman,Teodoro S.
author_sort Amongero,Marcela
title Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone
title_short Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone
title_full Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone
title_fullStr Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone
title_full_unstemmed Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone
title_sort chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (r)-carvone
description The synthesis of a series of chiral secondary alcohols derived from (R)-carvone, and the stereochemical outcome of their reaction with (±)-ibuprofen, is reported. The racemic drug was transformed into the corresponding diastereomeric esters mediated by DCC/DMAP, affording up to 5.7:1 diastereomeric ratios of the esters derived from either (S)- or (R)-ibuprofen, depending on the type of chiral auxiliary employed.
publisher Sociedade Brasileira de Química
publishDate 2010
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000600011
work_keys_str_mv AT amongeromarcela chiralauxiliarymediatedenantioenrichmentofibuprofenundersteglichconditionswithsecondaryalcoholsderivedfromrcarvone
AT visnovezkydamian chiralauxiliarymediatedenantioenrichmentofibuprofenundersteglichconditionswithsecondaryalcoholsderivedfromrcarvone
AT kaufmanteodoros chiralauxiliarymediatedenantioenrichmentofibuprofenundersteglichconditionswithsecondaryalcoholsderivedfromrcarvone
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