ArticleChemical science2021
Epoc group: transformable protecting group with gold(iii)-catalyzed fluorene formation.
Article in Chemical science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- TfOH-Promoted Cascade Reaction of Nitriles and 1,5-Enynes: An Efficient Route to Amido-Functionalized Fluorenes.The Journal of organic chemistry · 2025Article
- A practical method for the synthesis of small peptides using DCC and HOBt as activators in HRSC advances · 2024Article
- Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications.Chemical reviews · 2023Review
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Authors and funding
3 authors.
Funding
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Abstract
This study presents the novel concept of a transformable protecting group, which changes its properties through structural transformation. Based on this concept, we developed a 2-(2-ethynylphenyl)-2-(5-methylfuran-2-yl)-ethoxycarbonyl (Epoc) group. The Epoc group was transformed into an Fmoc-like structure with gold(iii)-catalyzed fluorene formation and was removable under Fmoc-like mild basic conditions post-transformation even though it was originally stable under strongly basic conditions. As an application for organic synthesis, the Epoc group provides the novel orthogonality of gold(iii)-labile protecting groups in solid-phase peptide synthesis. In addition, the high turnover number of fluorene formation in aqueous media is suggestive of the applicability of the Epoc group to biological systems.
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