Synthesis of optically active derivatives of bicyclic chiral diols with C2 symmetry

Autores
Zacconi, Flavia Cristina Milagro; Koll, Liliana Cristina; Podestá, Julio Cesar
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
This paper reports efficient procedures for the preparation of optically active dibromide, diazide, diamine, and unsaturated diesters derived from a chiral bicyclic diol with C2 symmetry namely (11R,12R)-9,10-dihydro- 9,10-ethaneanthracene-11,12-dimethanol 3. Esterification of 3 with saturated and unsaturated carboxylic acids and acids chlorides leads to the corresponding normal-, olefinic- and acetylenic diesters in average yields of 81%. Also more efficient techniques for the preparation of starting diol 3 in higher yields as well as for a very simple separation of DCU (N,N′-dicyclohexylurea) from reactions carried out following the DCC/DMAP method are described. © 2010 Elsevier Ltd. All rights reserved.
Fil: Zacconi, Flavia Cristina Milagro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Koll, Liliana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Materia
Bicyclic Chiral Diols
C2 Symmetry
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/64014
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of optically active derivatives of bicyclic chiral diols with C2 symmetryZacconi, Flavia Cristina MilagroKoll, Liliana CristinaPodestá, Julio CesarBicyclic Chiral DiolsC2 Symmetryhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1This paper reports efficient procedures for the preparation of optically active dibromide, diazide, diamine, and unsaturated diesters derived from a chiral bicyclic diol with C2 symmetry namely (11R,12R)-9,10-dihydro- 9,10-ethaneanthracene-11,12-dimethanol 3. Esterification of 3 with saturated and unsaturated carboxylic acids and acids chlorides leads to the corresponding normal-, olefinic- and acetylenic diesters in average yields of 81%. Also more efficient techniques for the preparation of starting diol 3 in higher yields as well as for a very simple separation of DCU (N,N′-dicyclohexylurea) from reactions carried out following the DCC/DMAP method are described. © 2010 Elsevier Ltd. All rights reserved.Fil: Zacconi, Flavia Cristina Milagro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Koll, Liliana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaPergamon-Elsevier Science Ltd2011-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/64014Zacconi, Flavia Cristina Milagro; Koll, Liliana Cristina; Podestá, Julio Cesar; Synthesis of optically active derivatives of bicyclic chiral diols with C2 symmetry; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 22; 1; 1-2011; 40-460957-4166CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0957416610008530info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetasy.2010.12.012info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:53:46Zoai:ri.conicet.gov.ar:11336/64014instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:53:46.384CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of optically active derivatives of bicyclic chiral diols with C2 symmetry
title Synthesis of optically active derivatives of bicyclic chiral diols with C2 symmetry
spellingShingle Synthesis of optically active derivatives of bicyclic chiral diols with C2 symmetry
Zacconi, Flavia Cristina Milagro
Bicyclic Chiral Diols
C2 Symmetry
title_short Synthesis of optically active derivatives of bicyclic chiral diols with C2 symmetry
title_full Synthesis of optically active derivatives of bicyclic chiral diols with C2 symmetry
title_fullStr Synthesis of optically active derivatives of bicyclic chiral diols with C2 symmetry
title_full_unstemmed Synthesis of optically active derivatives of bicyclic chiral diols with C2 symmetry
title_sort Synthesis of optically active derivatives of bicyclic chiral diols with C2 symmetry
dc.creator.none.fl_str_mv Zacconi, Flavia Cristina Milagro
Koll, Liliana Cristina
Podestá, Julio Cesar
author Zacconi, Flavia Cristina Milagro
author_facet Zacconi, Flavia Cristina Milagro
Koll, Liliana Cristina
Podestá, Julio Cesar
author_role author
author2 Koll, Liliana Cristina
Podestá, Julio Cesar
author2_role author
author
dc.subject.none.fl_str_mv Bicyclic Chiral Diols
C2 Symmetry
topic Bicyclic Chiral Diols
C2 Symmetry
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv This paper reports efficient procedures for the preparation of optically active dibromide, diazide, diamine, and unsaturated diesters derived from a chiral bicyclic diol with C2 symmetry namely (11R,12R)-9,10-dihydro- 9,10-ethaneanthracene-11,12-dimethanol 3. Esterification of 3 with saturated and unsaturated carboxylic acids and acids chlorides leads to the corresponding normal-, olefinic- and acetylenic diesters in average yields of 81%. Also more efficient techniques for the preparation of starting diol 3 in higher yields as well as for a very simple separation of DCU (N,N′-dicyclohexylurea) from reactions carried out following the DCC/DMAP method are described. © 2010 Elsevier Ltd. All rights reserved.
Fil: Zacconi, Flavia Cristina Milagro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Koll, Liliana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
description This paper reports efficient procedures for the preparation of optically active dibromide, diazide, diamine, and unsaturated diesters derived from a chiral bicyclic diol with C2 symmetry namely (11R,12R)-9,10-dihydro- 9,10-ethaneanthracene-11,12-dimethanol 3. Esterification of 3 with saturated and unsaturated carboxylic acids and acids chlorides leads to the corresponding normal-, olefinic- and acetylenic diesters in average yields of 81%. Also more efficient techniques for the preparation of starting diol 3 in higher yields as well as for a very simple separation of DCU (N,N′-dicyclohexylurea) from reactions carried out following the DCC/DMAP method are described. © 2010 Elsevier Ltd. All rights reserved.
publishDate 2011
dc.date.none.fl_str_mv 2011-01
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/64014
Zacconi, Flavia Cristina Milagro; Koll, Liliana Cristina; Podestá, Julio Cesar; Synthesis of optically active derivatives of bicyclic chiral diols with C2 symmetry; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 22; 1; 1-2011; 40-46
0957-4166
CONICET Digital
CONICET
url http://hdl.handle.net/11336/64014
identifier_str_mv Zacconi, Flavia Cristina Milagro; Koll, Liliana Cristina; Podestá, Julio Cesar; Synthesis of optically active derivatives of bicyclic chiral diols with C2 symmetry; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 22; 1; 1-2011; 40-46
0957-4166
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0957416610008530
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetasy.2010.12.012
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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