Details

Autor(en) / Beteiligte

• Tian, Jun‐Jie
• Li, Rui‐Rui
• Tian, Gui‐Xiu
• Wang, Xiao‐Chen

Titel

Enantioselective C3‐Allylation of Pyridines via Tandem Borane and Palladium Catalysis

Ist Teil von

• Angewandte Chemie International Edition, 2023-08, Vol.62 (34), p.e202307697-n/a

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2023

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Herein, we report a one‐pot method for enantioselective C−H allylation of pyridines at C3 via tandem borane and palladium catalysis. This method involves borane‐catalyzed pyridine hydroboration to generate dihydropyridines, then palladium‐catalyzed enantioselective allylation of the dihydropyridines with allylic esters, and finally air oxidation of the allylated dihydropyridines to afford the products. This method enables the introduction of an allylic group at C3 with excellent regio‐ and enantioselectivities. A one‐pot, three‐step method for highly enantioselective C3‐allylation reactions of pyridines was developed. The method involved borane‐catalyzed dearomative pyridine hydroboration, palladium‐catalyzed enantioselective allylation of the dearomatized intermediate, and finally oxidation by air. The method was applicable to a broad range of pyridines, N‐heteroarenes, and allylic esters.