A mild and efficient telescoped procedure for the stereoselective alkenylation of simple, non-activated amides using LiCH2SiMe3 and carbonyl compounds as surrogates of alkenyllithium reagents is reported. Our methodology relies on the formation of stable tetrahedral intermediates, which, upon collapse into highly reactive lithium enolates in a solvent-dependent fashion, allows for the assembly of α,β-unsaturated ketones in a single synthetic operation with high stereoselectivity.
One-Pot, Telescoped Alkenylation of Amides via Stable Tetrahedral Intermediates as Lithium Enolate Precursors
Ghinato, Simone;Meazzo, Carolina;De Nardi, Federica;Maranzana, Andrea;Blangetti, Marco
;Prandi, Cristina
2023-01-01
Abstract
A mild and efficient telescoped procedure for the stereoselective alkenylation of simple, non-activated amides using LiCH2SiMe3 and carbonyl compounds as surrogates of alkenyllithium reagents is reported. Our methodology relies on the formation of stable tetrahedral intermediates, which, upon collapse into highly reactive lithium enolates in a solvent-dependent fashion, allows for the assembly of α,β-unsaturated ketones in a single synthetic operation with high stereoselectivity.
File in questo prodotto:
| File | Dimensione | Formato | |
|---|---|---|---|
|
acs.orglett.3c01269.pdf
Accesso aperto
Descrizione: manuscript
Tipo di file:
PDF EDITORIALE
Dimensione
1.89 MB
Formato
Adobe PDF
|
1.89 MB | Adobe PDF | Visualizza/Apri |
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
