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Isopropenyl phosphate as an atom efficient reagent for phosphorylation of alcohols with catalytic base

The atom efficient transesterification of phosphate esters with catalytic base was investigated using an isopropenyl leaving group, generating acetone as the only by-product. The reaction proceeds in good yields at room temperature, with excellent chemoselectivity towards primary alcohols. Mechanist...

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Detalles Bibliográficos
Autores principales: Wéry, Jens, Beckers, Igor, De Vos, Dirk E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10170494/
https://www.ncbi.nlm.nih.gov/pubmed/37180006
http://dx.doi.org/10.1039/d3ra02293e
Descripción
Sumario:The atom efficient transesterification of phosphate esters with catalytic base was investigated using an isopropenyl leaving group, generating acetone as the only by-product. The reaction proceeds in good yields at room temperature, with excellent chemoselectivity towards primary alcohols. Mechanistic insights were obtained by obtaining kinetic data using in operando NMR-spectroscopy.