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

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.

SUBMITTER: Zheng Y

PROVIDER: S-EPMC9968317 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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

Zheng Yang Y Zhang Wen-Yun WY Gu Qing Q Zheng Chao C You Shu-Li SL

Nature communications 20230225 1

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*CoI<sub>2</sub>CO. Combined experimental and computat ...[more]

PMID: 36841798

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