Catalytic enantioselective nucleophilic desymmetrization of phosphonate esters.
Journal
Nature chemistry
ISSN: 1755-4349
Titre abrégé: Nat Chem
Pays: England
ID NLM: 101499734
Informations de publication
Date de publication:
May 2023
May 2023
Historique:
received:
06
08
2021
accepted:
20
02
2023
medline:
2
5
2023
pubmed:
2
5
2023
entrez:
1
5
2023
Statut:
ppublish
Résumé
Molecules that contain a stereogenic phosphorus atom are crucial to medicine, agrochemistry and catalysis. While methods are available for the selective construction of various chiral organophosphorus compounds, catalytic enantioselective approaches for their synthesis are far less common. Given the vastness of possible substituent combinations around a phosphorus atom, protocols for their preparation should also be divergent, providing facile access not only to one but to many classes of phosphorus compounds. Here we introduce a catalytic and enantioselective strategy for the preparation of an enantioenriched phosphorus(V) centre that can be diversified enantiospecifically to a wide range of biologically relevant phosphorus(V) compounds. The process, which involves an enantioselective nucleophilic substitution catalysed by a superbasic bifunctional iminophosphorane catalyst, can accommodate a wide range of carbon substituents at phosphorus. The resulting stable, yet versatile, synthetic intermediates can be combined with a multitude of medicinally relevant O-, N- and S-based nucleophiles.
Identifiants
pubmed: 37127757
doi: 10.1038/s41557-023-01165-6
pii: 10.1038/s41557-023-01165-6
pmc: PMC10159838
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
714-721Subventions
Organisme : RCUK | Engineering and Physical Sciences Research Council (EPSRC)
ID : EP/L015838/1
Organisme : Canadian Network for Research and Innovation in Machining Technology, Natural Sciences and Engineering Research Council of Canada (NSERC Canadian Network for Research and Innovation in Machining Technology)
ID : PGSD3-532666-2019
Organisme : EC | EU Framework Programme for Research and Innovation H2020 | H2020 Priority Excellent Science | H2020 Marie Skłodowska-Curie Actions (H2020 Excellent Science - Marie Skłodowska-Curie Actions)
ID : 10133408
Informations de copyright
© 2023. The Author(s), under exclusive licence to Springer Nature Limited.
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