Accessing Axially and Centrally Chiral N-Arylindoles Merging n → π* Interaction with Organocatalyzed
Qin Shi1, Lu Ruan1, Ming-Fei Duan1
1School of Pharmacy, Anhui University of Chinese Medicine, Hefei 230012, China.
Abstract:
Herein, we present a chiral phosphoric acid-catalyzed dynamic kinetic resolution strategy that achieves precise control over both axial and point chiralities in N-arylindoles by merging the N(sp3)···C═O n → π* interaction with the Pictet-Spengler-type cyclization. A series of centrally chiral dihydropyrrolo[1,2-a]quinoxaline-fused N-arylindole atropisomers were obtained with high to excellent results (up to 99% yield, >20:1 dr and 98% ee). The methodology exhibits scalability, mild conditions, and good functional group tolerance, making it a promising option for research into multiple chiral N-containing polycyclic frameworks.
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