Synthetic applications of chiral unsaturated epoxy alcohols prepared by sharpless asymmetric epoxidation

An overview of the synthesis and applications of chiral 2,3-epoxy alcohols containing unsaturated chains is presented. One of the fundamental synthetic routes to these compounds is Sharpless asymmetric epoxidation, which is reliable, highly chemoselective and enables easy prediction of the product e...

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Detalles Bibliográficos
Autores: Riera i Escalé, Antoni, Moreno, María
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2010
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/20788
Acceso en línea:https://hdl.handle.net/2445/20788
Access Level:acceso abierto
Palabra clave:Síntesi asimètrica
Epòxids
Alquens
Asymmetric synthesis
Epoxy compounds
Alkenes
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spelling Synthetic applications of chiral unsaturated epoxy alcohols prepared by sharpless asymmetric epoxidationRiera i Escalé, AntoniMoreno, MaríaSíntesi asimètricaEpòxidsAlquensAsymmetric synthesisEpoxy compoundsAlkenesAn overview of the synthesis and applications of chiral 2,3-epoxy alcohols containing unsaturated chains is presented. One of the fundamental synthetic routes to these compounds is Sharpless asymmetric epoxidation, which is reliable, highly chemoselective and enables easy prediction of the product enantioselectivity. Thus, unsaturated epoxy alcohols are readily obtained by selective oxidation of the allylic double bond in the presence of other carbon-carbon double or triple bonds. The wide availability of epoxy alcohols with unsaturated chains, the versatility of the epoxy alcohol functionality (e.g. regio- and stereo-selective ring opening; oxidation; and reduction), and the arsenal of established alkene chemistries, make unsaturated epoxy alcohols powerful starting materials for the synthesis of complex targets such as biologically active molecules. The popularization of ring-closing metathesis has further increased their value, making them excellent precursors to cyclic compounds.MDPI Publishing201120112010info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersion33 p.application/pdfhttps://hdl.handle.net/2445/20788Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésReproducció del document publicat a: http://dx.doi.org/10.3390/molecules15021041Molecules 2010, 15(2), 1041-1073http://dx.doi.org/10.3390/molecules15021041cc-by, (c) Riera et al., 2010http://creativecommons.org/licenses/by/3.0/info:eu-repo/semantics/openAccessoai:recercat.cat:2445/207882026-05-29T05:05:01Z
dc.title.none.fl_str_mv Synthetic applications of chiral unsaturated epoxy alcohols prepared by sharpless asymmetric epoxidation
title Synthetic applications of chiral unsaturated epoxy alcohols prepared by sharpless asymmetric epoxidation
spellingShingle Synthetic applications of chiral unsaturated epoxy alcohols prepared by sharpless asymmetric epoxidation
Riera i Escalé, Antoni
Síntesi asimètrica
Epòxids
Alquens
Asymmetric synthesis
Epoxy compounds
Alkenes
title_short Synthetic applications of chiral unsaturated epoxy alcohols prepared by sharpless asymmetric epoxidation
title_full Synthetic applications of chiral unsaturated epoxy alcohols prepared by sharpless asymmetric epoxidation
title_fullStr Synthetic applications of chiral unsaturated epoxy alcohols prepared by sharpless asymmetric epoxidation
title_full_unstemmed Synthetic applications of chiral unsaturated epoxy alcohols prepared by sharpless asymmetric epoxidation
title_sort Synthetic applications of chiral unsaturated epoxy alcohols prepared by sharpless asymmetric epoxidation
dc.creator.none.fl_str_mv Riera i Escalé, Antoni
Moreno, María
author Riera i Escalé, Antoni
author_facet Riera i Escalé, Antoni
Moreno, María
author_role author
author2 Moreno, María
author2_role author
dc.subject.none.fl_str_mv Síntesi asimètrica
Epòxids
Alquens
Asymmetric synthesis
Epoxy compounds
Alkenes
topic Síntesi asimètrica
Epòxids
Alquens
Asymmetric synthesis
Epoxy compounds
Alkenes
description An overview of the synthesis and applications of chiral 2,3-epoxy alcohols containing unsaturated chains is presented. One of the fundamental synthetic routes to these compounds is Sharpless asymmetric epoxidation, which is reliable, highly chemoselective and enables easy prediction of the product enantioselectivity. Thus, unsaturated epoxy alcohols are readily obtained by selective oxidation of the allylic double bond in the presence of other carbon-carbon double or triple bonds. The wide availability of epoxy alcohols with unsaturated chains, the versatility of the epoxy alcohol functionality (e.g. regio- and stereo-selective ring opening; oxidation; and reduction), and the arsenal of established alkene chemistries, make unsaturated epoxy alcohols powerful starting materials for the synthesis of complex targets such as biologically active molecules. The popularization of ring-closing metathesis has further increased their value, making them excellent precursors to cyclic compounds.
publishDate 2010
dc.date.none.fl_str_mv 2010
2011
2011
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/20788
url https://hdl.handle.net/2445/20788
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Reproducció del document publicat a: http://dx.doi.org/10.3390/molecules15021041
Molecules 2010, 15(2), 1041-1073
http://dx.doi.org/10.3390/molecules15021041
dc.rights.none.fl_str_mv cc-by, (c) Riera et al., 2010
http://creativecommons.org/licenses/by/3.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by, (c) Riera et al., 2010
http://creativecommons.org/licenses/by/3.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 33 p.
application/pdf
dc.publisher.none.fl_str_mv MDPI Publishing
publisher.none.fl_str_mv MDPI Publishing
dc.source.none.fl_str_mv Articles publicats en revistes (Química Inorgànica i Orgànica)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,81155

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