Cobalt(III)-catalyzed asymmetric ring-opening of 7-oxabenzonorbornadienes via indole C–H functionalization

Yang Zheng, Wen-Yun Zhang, Qing Gu, Chao Zheng () and Shu-Li You ()
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Yang Zheng: Chinese Academy of Sciences
Wen-Yun Zhang: Chinese Academy of Sciences
Qing Gu: Chinese Academy of Sciences
Chao Zheng: Chinese Academy of Sciences
Shu-Li You: Chinese Academy of Sciences

Nature Communications, 2023, vol. 14, issue 1, 1-9

Abstract: Abstract Asymmetric ring-opening of 7-oxabenzonorbornadienes is achieved via Co-catalyzed indole C–H functionalization. The utilization of chiral Co-catalyst consisting of a binaphthyl-derived trisubstituted cyclopentadienyl ligand resulted in high yields (up to 99%) and excellent enantioselectivity (>99% ee) for the target products with tolerance for diverse functional groups. Opposite diastereoselectivities are obtained with chiral Co-catalyst or Cp*CoI2CO. Combined experimental and computational studies suggest β-oxygen elimination being the selectivity-determining step of the reaction. Meanwhile, the reactions of 7-azabenzonorbornadiene could also be executed in a diastereodivergent manner.

Date: 2023
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DOI: 10.1038/s41467-023-36723-6

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