All-Carbon Quaternary Stereocenters α to Azaarenes via Radical-Based Asymmetric Olefin Difunctionalization

Yanli YinYanli Yin, Yunqiang Li, Théo P. Gonçalves, Qiangqiang Zhan, Guanghui Wang, Xiaowei Zhao, Baokun Qiao, Kuo-Wei Huang, Zhiyong Jiang
Journal of the American Chemical Society, (2020)


Hydrocarbons, Stereoselectivity, Catalysts, Aromatic compounds, Solvents


​A radical-based asymmetric olefin difunctionalization strategy for rapidly forging all-carbon quaternary stereocenters α to diverse azaarenes is reported. Under cooperative photoredox and chiral Brønsted acid catalysis, cyclopropylamines with α-branched 2-vinylazaarenes can undergo a sequential two-step radical process, furnishing various valuable chiral azaarene-substituted cyclopentanes. The use of the rigid and confined C2-symmetric imidodiphosphoric acid catalysts achieves high enantio- and diastereo-selectivities for these asymmetric [3 + 2] cycloadditions.



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