Ni-Catalyzed Asymmetric Reductive Carbonyl Addition of N-Arylindole-2-carbaldehydes with Aryl Halides
Changqiu Guo1, Yanxin Gu1, Li Li1
1State Key Laboratory of Chemo and Biosensing, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China.
Abstract:
The catalytic construction of axial chirality via asymmetric reductive carbonyl addition by carbon electrophiles remains underexplored. Herein, we report a nickel-catalyzed enantioselective reductive carbonyl addition of N-arylindole-2-carbaldehydes with aryl halides that simultaneously forges central and C-N axial chirality. This method provides efficient access to a range of axially chiral N-arylindole alcohols in high yields with excellent enantioselectivity under mild conditions. The reaction tolerates a variety of substituents on both the aryl halide and the indole aldehyde. Furthermore, the synthetic utility of this protocol is demonstrated through gram-scale synthesis and the versatile functionalization of the hydroxyl group, underscoring its potential as a robust platform for synthesizing enantioenriched, axially chiral scaffolds.
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