Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses

Pyranosic enuloses were subjected to Horner-Wadsworth-Emmons (HWE) conditions using the enolate of dimethyl(methoxycarbonyl)methyl phosphonate and its ethyl analogue. 3-O-Phosphorylation of the products as well as an unusual stereospecificity were observed. A mechanism involving a phosphonate-phosph...

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Detalles Bibliográficos
Autor principal: Moradei, Oscar Miguel
Publicado: 1997
Materias:
sugar phosphate
article
carbohydrate synthesis
drug synthesis
in vitro study
methodology
nuclear magnetic resonance spectroscopy
priority journal
reaction analysis
stereochemistry
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v53_n22_p7397_Moradei
http://hdl.handle.net/20.500.12110/paper_00404020_v53_n22_p7397_Moradei
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_00404020_v53_n22_p7397_Moradei
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spelling paper:paper_00404020_v53_n22_p7397_Moradei2023-06-08T15:04:12Z Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses Moradei, Oscar Miguel sugar phosphate article carbohydrate synthesis drug synthesis in vitro study methodology nuclear magnetic resonance spectroscopy priority journal reaction analysis stereochemistry Pyranosic enuloses were subjected to Horner-Wadsworth-Emmons (HWE) conditions using the enolate of dimethyl(methoxycarbonyl)methyl phosphonate and its ethyl analogue. 3-O-Phosphorylation of the products as well as an unusual stereospecificity were observed. A mechanism involving a phosphonate-phosphate like rearrangement through a five member intermediate followed by benzoate elimination is proposed. Fil:Moradei, O.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 1997 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v53_n22_p7397_Moradei http://hdl.handle.net/20.500.12110/paper_00404020_v53_n22_p7397_Moradei
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic sugar phosphate
article
carbohydrate synthesis
drug synthesis
in vitro study
methodology
nuclear magnetic resonance spectroscopy
priority journal
reaction analysis
stereochemistry
spellingShingle sugar phosphate
article
carbohydrate synthesis
drug synthesis
in vitro study
methodology
nuclear magnetic resonance spectroscopy
priority journal
reaction analysis
stereochemistry
Moradei, Oscar Miguel
Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses
topic_facet sugar phosphate
article
carbohydrate synthesis
drug synthesis
in vitro study
methodology
nuclear magnetic resonance spectroscopy
priority journal
reaction analysis
stereochemistry
description Pyranosic enuloses were subjected to Horner-Wadsworth-Emmons (HWE) conditions using the enolate of dimethyl(methoxycarbonyl)methyl phosphonate and its ethyl analogue. 3-O-Phosphorylation of the products as well as an unusual stereospecificity were observed. A mechanism involving a phosphonate-phosphate like rearrangement through a five member intermediate followed by benzoate elimination is proposed.
author Moradei, Oscar Miguel
author_facet Moradei, Oscar Miguel
author_sort Moradei, Oscar Miguel
title Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses
title_short Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses
title_full Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses
title_fullStr Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses
title_full_unstemmed Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses
title_sort anomalous horner-wadsworth-emmons reactions on 3,4-enuloses
publishDate 1997
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v53_n22_p7397_Moradei
http://hdl.handle.net/20.500.12110/paper_00404020_v53_n22_p7397_Moradei
work_keys_str_mv AT moradeioscarmiguel anomaloushornerwadsworthemmonsreactionson34enuloses
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