Palladium-Catalyzed Enantioselective γ-Arylation of ß,γ-Unsaturated Butenolides.
Angew Chem Int Ed Engl
; 61(23): e202202046, 2022 06 07.
Article
en En
| MEDLINE
| ID: mdl-35315964
ABSTRACT
γ-Butenolide and γ-butyrolactone scaffolds are two types of important core structures in numerous natural products and bioactive targets. However, methods to construct the chiral quaternary arylated γ-butenolide are rarely explored. We herein report an efficient Pd-catalyzed enantioselective γ-arylation of ß,γ-unsaturated butenolides with aryl bromides, which shows high γ-selectivity, good functional group tolerance and excellent enantioselectivity. Notably, this protocol also allows for facile construction of tricyclic tetrahydroindolines and tetrahydroisoquinolinones in one step. DFT calculations are consistent with the experimental results, suggesting that the γ-arylation is favoured over the α-arylation. Finally, this method is applied to the rapid synthesis of natural product (R)-(+)-boivinianinâ
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Palabras clave
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Paladio
/
4-Butirolactona
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Año:
2022
Tipo del documento:
Article
País de afiliación:
China