Study of the Stereoselectivity of the Nucleophilic Epoxidation of 3-Hydroxy-2- methylene Esters

The diastereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2-methylene esters has been studied. The 3-hydroxy-2-methylene esters were obtained through a Morita–Baylis–Hillman reaction. The resulting epoxyesters were treated with thiophenol for transformation into 2,3-dihydroxy-2-((phenylt...

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Published in:Tetrahedron
Main Authors: Latorre, Antonio, Sáez Cases, José Antonio, Rodríguez, Santiago, González, Florenci
Format: Article in Journal/Newspaper
Language:English
Published: Elsevier 2014
Subjects:
chemical reaction
epoxidation
Morita Baylis Hillman reaction
nucleophilicity
stereochemistry
carbonic acid derivative
ester derivative
thiophenol derivative
Carbonic acid
Online Access:http://hdl.handle.net/10234/88869
https://doi.org/10.1016/j.tet.2013.11.014
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spelling ftunivjaumeirep:oai:repositori.uji.es:10234/88869 2024-09-09T19:36:03+00:00 Study of the Stereoselectivity of the Nucleophilic Epoxidation of 3-Hydroxy-2- methylene Esters Latorre, Antonio Sáez Cases, José Antonio Rodríguez, Santiago González, Florenci 2014-03-31T07:11:48Z application/pdf http://hdl.handle.net/10234/88869 https://doi.org/10.1016/j.tet.2013.11.014 eng eng Elsevier Tetrahedron Volume 70, Issue 1, 7 January 2014 http://www.sciencedirect.com/science/article/pii/S004040201301702X LATORRE, Antonio, et al. Study of the stereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2-methylene esters. Tetrahedron, 2014, 70.1: 97-102. http://hdl.handle.net/10234/88869 http://dx.doi.org/10.1016/j.tet.2013.11.014 Copyright © 2014 Elsevier B.V. http://rightsstatements.org/vocab/InC/1.0/ info:eu-repo/semantics/openAccess chemical reaction epoxidation Morita Baylis Hillman reaction nucleophilicity stereochemistry carbonic acid derivative ester derivative thiophenol derivative info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion info:eu-repo/semantics/acceptedVersion 2014 ftunivjaumeirep https://doi.org/10.1016/j.tet.2013.11.014 2024-06-18T14:26:31Z The diastereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2-methylene esters has been studied. The 3-hydroxy-2-methylene esters were obtained through a Morita–Baylis–Hillman reaction. The resulting epoxyesters were treated with thiophenol for transformation into 2,3-dihydroxy-2-((phenylthio)methyl), which upon treatment with triphosgene afforded the corresponding cyclic carbonates. Article in Journal/Newspaper Carbonic acid Repositori Universitat Jaume I (Repositorio UJI) Tetrahedron 70 1 97 102
institution Open Polar
collection Repositori Universitat Jaume I (Repositorio UJI)
op_collection_id ftunivjaumeirep
language English
topic chemical reaction
epoxidation
Morita Baylis Hillman reaction
nucleophilicity
stereochemistry
carbonic acid derivative
ester derivative
thiophenol derivative
spellingShingle chemical reaction
epoxidation
Morita Baylis Hillman reaction
nucleophilicity
stereochemistry
carbonic acid derivative
ester derivative
thiophenol derivative
Latorre, Antonio
Sáez Cases, José Antonio
Rodríguez, Santiago
González, Florenci
Study of the Stereoselectivity of the Nucleophilic Epoxidation of 3-Hydroxy-2- methylene Esters
topic_facet chemical reaction
epoxidation
Morita Baylis Hillman reaction
nucleophilicity
stereochemistry
carbonic acid derivative
ester derivative
thiophenol derivative
description The diastereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2-methylene esters has been studied. The 3-hydroxy-2-methylene esters were obtained through a Morita–Baylis–Hillman reaction. The resulting epoxyesters were treated with thiophenol for transformation into 2,3-dihydroxy-2-((phenylthio)methyl), which upon treatment with triphosgene afforded the corresponding cyclic carbonates.
format Article in Journal/Newspaper
author Latorre, Antonio
Sáez Cases, José Antonio
Rodríguez, Santiago
González, Florenci
author_facet Latorre, Antonio
Sáez Cases, José Antonio
Rodríguez, Santiago
González, Florenci
author_sort Latorre, Antonio
title Study of the Stereoselectivity of the Nucleophilic Epoxidation of 3-Hydroxy-2- methylene Esters
title_short Study of the Stereoselectivity of the Nucleophilic Epoxidation of 3-Hydroxy-2- methylene Esters
title_full Study of the Stereoselectivity of the Nucleophilic Epoxidation of 3-Hydroxy-2- methylene Esters
title_fullStr Study of the Stereoselectivity of the Nucleophilic Epoxidation of 3-Hydroxy-2- methylene Esters
title_full_unstemmed Study of the Stereoselectivity of the Nucleophilic Epoxidation of 3-Hydroxy-2- methylene Esters
title_sort study of the stereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2- methylene esters
publisher Elsevier
publishDate 2014
url http://hdl.handle.net/10234/88869
https://doi.org/10.1016/j.tet.2013.11.014
genre Carbonic acid
genre_facet Carbonic acid
op_relation Tetrahedron Volume 70, Issue 1, 7 January 2014
http://www.sciencedirect.com/science/article/pii/S004040201301702X
LATORRE, Antonio, et al. Study of the stereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2-methylene esters. Tetrahedron, 2014, 70.1: 97-102.
http://hdl.handle.net/10234/88869
http://dx.doi.org/10.1016/j.tet.2013.11.014
op_rights Copyright © 2014 Elsevier B.V.
http://rightsstatements.org/vocab/InC/1.0/
info:eu-repo/semantics/openAccess
op_doi https://doi.org/10.1016/j.tet.2013.11.014
container_title Tetrahedron
container_volume 70
container_issue 1
container_start_page 97
op_container_end_page 102
_version_ 1809905323698290688

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