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
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
Descripción
Sumario: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.

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