Skip to Main Content (Press Enter)

Logo UNITO
  • ×
  • Home
  • Pubblicazioni
  • Progetti
  • Persone
  • Competenze
  • Settori
  • Strutture
  • Terza Missione

UNI-FIND
Logo UNITO

|

UNI-FIND

unito.it
  • ×
  • Home
  • Pubblicazioni
  • Progetti
  • Persone
  • Competenze
  • Settori
  • Strutture
  • Terza Missione
  1. Pubblicazioni

4‐Methyltetrahydropyran: a Versatile Alternative Solvent for the Preparation of Chiral BINOL Catalysts and the Asymmetric Alkylation of Aldehydes

Articolo
Data di Pubblicazione:
2024
Abstract:
We herein report that the highly hydrophobic ether 4-MeTHP constitutes a promising resource for the development of sustainable synthetic methodologies grounded on the use of organometallic reagents. The beneficial effects of 4-MeTHP as reaction media are illustrated in the organolithium-promoted anionic ortho-Fries rearrangement of 1,1’-bi-2-naphthol (BINOL)-based carbamates under bench-type conditions. The use of 4-MeTHP induces a remarkable and unexpected stability of the organolithiums species, enabling the efficient preparation of chiral (bis)carboxamide catalysts. Furthermore, superior performances of 4-MeTHP than other environmentally responsible solvents are observed using the synthesized BINOL catalysts in the asymmetric addition of organozinc reagents to aldehydes. Spectroscopic studies in solution suggest that 4-MeTHP plays a key role in these reactions by inducing the preferential formation of a reactive monomeric dinuclear complex. This methodology allows for the asymmetric assembly of enantioenriched secondary alcohols in good yields and high stereoselectivity, working at 0 °C and under air.
Tipologia CRIS:
03A-Articolo su Rivista
Keywords:
4-methyltetrahydropyran, Fries rearrangement, alkali metal, BINOL, asymmetric alkylation
Elenco autori:
Marra, Francesco; De Nardi, Federica; Rossi, Federica; Priola, Emanuele; Prandi, Cristina; Blangetti, Marco
Autori di Ateneo:
BLANGETTI Marco
PRANDI Cristina
PRIOLA Emanuele
Link alla scheda completa:
https://iris.unito.it/handle/2318/1978591
Link al Full Text:
https://iris.unito.it/retrieve/handle/2318/1978591/1301432/manuscript_submitted.pdf
https://iris.unito.it/retrieve/handle/2318/1978591/1499094/Eur%20J%20Org%20Chem%20-%202024%20OA.pdf
Pubblicato in:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Journal
Progetto:
Unlocking Greener Metal-assisted Synthetic Tactics by Sustainable Solvents and Technologies - Finanziamento dell’Unione Europea – NextGenerationEU – missione 4, componente 2, investimento 1.1.
  • Dati Generali
  • Aree Di Ricerca

Dati Generali

URL

https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202400313

Aree Di Ricerca

Settori (4)


PE5_17 - Organic chemistry - (2022)

PIANETA TERRA, AMBIENTE, CLIMA, ENERGIA e SOSTENIBILITA' - Chimica e Ambiente

SCIENZE MATEMATICHE, CHIMICHE, FISICHE - Chimica Organica e Industriale

SCIENZE MATEMATICHE, CHIMICHE, FISICHE - Materiali Avanzati
  • Utilizzo dei cookie

Realizzato con VIVO | Designed by Cineca | 25.5.0.1