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...

Descripción completa

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:
Chemistry
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
_version_ 1785039239679836160
author Wéry, Jens
Beckers, Igor
De Vos, Dirk E.
author_facet Wéry, Jens
Beckers, Igor
De Vos, Dirk E.
author_sort Wéry, Jens
collection PubMed
description 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.
format Online
Article
Text
id pubmed-10170494
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-101704942023-05-11 Isopropenyl phosphate as an atom efficient reagent for phosphorylation of alcohols with catalytic base Wéry, Jens Beckers, Igor De Vos, Dirk E. RSC Adv Chemistry 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. The Royal Society of Chemistry 2023-05-10 /pmc/articles/PMC10170494/ /pubmed/37180006 http://dx.doi.org/10.1039/d3ra02293e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Wéry, Jens
Beckers, Igor
De Vos, Dirk E.
Isopropenyl phosphate as an atom efficient reagent for phosphorylation of alcohols with catalytic base
title Isopropenyl phosphate as an atom efficient reagent for phosphorylation of alcohols with catalytic base
title_full Isopropenyl phosphate as an atom efficient reagent for phosphorylation of alcohols with catalytic base
title_fullStr Isopropenyl phosphate as an atom efficient reagent for phosphorylation of alcohols with catalytic base
title_full_unstemmed Isopropenyl phosphate as an atom efficient reagent for phosphorylation of alcohols with catalytic base
title_short Isopropenyl phosphate as an atom efficient reagent for phosphorylation of alcohols with catalytic base
title_sort isopropenyl phosphate as an atom efficient reagent for phosphorylation of alcohols with catalytic base
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10170494/
https://www.ncbi.nlm.nih.gov/pubmed/37180006
http://dx.doi.org/10.1039/d3ra02293e
work_keys_str_mv AT weryjens isopropenylphosphateasanatomefficientreagentforphosphorylationofalcoholswithcatalyticbase
AT beckersigor isopropenylphosphateasanatomefficientreagentforphosphorylationofalcoholswithcatalyticbase
AT devosdirke isopropenylphosphateasanatomefficientreagentforphosphorylationofalcoholswithcatalyticbase

Ejemplares similares