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...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autores principales: Moradei, O.M., Du Mortier, C.M., Cirelli, A.F.
Formato: JOUR
Materias:
sugar phosphate
article
carbohydrate synthesis
drug synthesis
in vitro study
methodology
nuclear magnetic resonance spectroscopy
priority journal
reaction analysis
stereochemistry
Acceso en línea: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 todo:paper_00404020_v53_n22_p7397_Moradei
record_format dspace
spelling todo:paper_00404020_v53_n22_p7397_Moradei2023-10-03T14:50:37Z Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses Moradei, O.M. Du Mortier, C.M. Cirelli, A.F. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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, O.M.
Du Mortier, C.M.
Cirelli, A.F.
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.
format JOUR
author Moradei, O.M.
Du Mortier, C.M.
Cirelli, A.F.
author_facet Moradei, O.M.
Du Mortier, C.M.
Cirelli, A.F.
author_sort Moradei, O.M.
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
url http://hdl.handle.net/20.500.12110/paper_00404020_v53_n22_p7397_Moradei
work_keys_str_mv AT moradeiom anomaloushornerwadsworthemmonsreactionson34enuloses
AT dumortiercm anomaloushornerwadsworthemmonsreactionson34enuloses
AT cirelliaf anomaloushornerwadsworthemmonsreactionson34enuloses
_version_ 1807316907094704128

Ejemplares similares