Cobalt(III)-catalyzed asymmetric ring-opening of 7-oxabenzonorbornadienes via indole C-H functionalization.
basic_science · Level V
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- Record sourced from PubMed, PMID 36841798.
- Also identified by DOI 10.1038/s41467-023-36723-6 and PMC identifier 9968317.
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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*CoI<sub>2</sub>CO. 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.