ArticleJournal of the American Chemical Society2021
Enantioselective Hydrothiolation: Diverging Cyclopropenes through Ligand Control.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
9 citing papers in PubMed.
- Stereoselective palladium-catalyzed carboetherification of cyclopropenesChemical science · 2026Article
- Bifunctional Iminophosphorane Superbases Enable the Highly Enantioselective Sulfa-Michael Addition to Fully Substituted Cyclopropene Carboxylic Acid Derivatives.Journal of the American Chemical Society · 2025Article
- Catalytic Markovnikov Hydrothiolation of Dehydroamino Acids: Unified Total Synthesis of Enteropeptin Sactipeptides.Journal of the American Chemical Society · 2025Article
- Chemo-, regio- and enantioselective hydroformylation of trisubstituted cyclopropenes: access to chiral quaternary cyclopropanes.Nature communications · 2024Article
- Total Synthesis and Stereochemical Assignment of Enteropeptin A.Journal of the American Chemical Society · 2024Article
- Copper-Phosphido Catalysis: Enantioselective Addition of Phosphines to Cyclopropenes.Angewandte Chemie (International ed. in English) · 2023Article
- Copper-Catalyzed Hydroamination: Enantioselective Addition of Pyrazoles to Cyclopropenes.Journal of the American Chemical Society · 2023Article
- Enantioselective Hydroalkoxylation of 1,3-Dienes via Ni-Catalysis.Journal of the American Chemical Society · 2023Article
- Preparation of Chiral Enantioenriched Densely Substituted Cyclopropyl Azoles, Amines, and Ethers via Formal SMolecules (Basel, Switzerland) · 2022Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
In this article, we advance Rh-catalyzed hydrothiolation through the divergent reactivity of cyclopropenes. Cyclopropenes undergo hydrothiolation to provide cyclopropyl sulfides or allylic sulfides. The choice of bisphosphine ligand dictates whether the pathway involves ring-retention or ring-opening. Mechanistic studies reveal the origin for this switchable selectivity. Our results suggest the two pathways share a common cyclopropyl-Rh(III) intermediate. Electron-rich Josiphos ligands promote direct reductive elimination from this intermediate to afford cyclopropyl sulfides in high enantio- and diastereoselectivities. Alternatively, atropisomeric ligands (such as DTBM-BINAP) enable ring-opening from the cyclopropyl-Rh(III) intermediate to generate allylic sulfides with high enantio- and regiocontrol.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.