ArticleChemical science2018
Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles.
Article in Chemical science, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Catalytic Enantioselective Dearomatizing [2,3]-Wittig Rearrangements Allow Divergent [2,3]-, [1,2]-, and Sommelet-Hauser-Type Products.Journal of the American Chemical Society · 2026Article
- Chiral phosphoric acid-catalyzed asymmetric epoxidation of alkenyl aza-heteroarenes using hydrogen peroxide.Nature communications · 2024Article
- Catalytic Enantioselective Intramolecular Oxa-Michael Reaction to α,β-Unsaturated Esters and Amides.Journal of the American Chemical Society · 2023Article
- Catalytic, Asymmetric Michael-Aldol Annulations via a Stereodivergent/Stereoconvergent Path Operating under Curtin-Hammett Control.Journal of the American Chemical Society · 2023Article
- Bifunctional Iminophosphorane-Catalyzed Enantioselective Nitroalkane Addition to Unactivated α,β-Unsaturated Esters.Angewandte Chemie (International ed. in English) · 2023Article
- Bifunctional Iminophosphorane-Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α,β-Unsaturated Amides.Journal of the American Chemical Society · 2022Article
- Tunable and Cooperative Catalysis for Enantioselective Pictet-Spengler Reaction with Varied Nitrogen-Containing Heterocyclic Carboxaldehydes.Angewandte Chemie (International ed. in English) · 2021Article
- Phosphorus-Containing Superbases: Recent Progress in the Chemistry of Electron-Abundant Phosphines and Phosphazenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Synthesis of β-Hydroxy α-Amino Acids Through Brønsted Base-CatalyzedThe Journal of organic chemistry · 2021Article
- A bifunctional iminophosphorane squaramide catalyzed enantioselective synthesis of hydroquinazolinesChemical science · 2021Article
- BIMP-Catalyzed 1,3-Prototropic Shift for the Highly Enantioselective Synthesis of Conjugated Cyclohexenones.Angewandte Chemie (International ed. in English) · 2020Article
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Authors and funding
6 authors.
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Abstract
The first enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles, enabled by a bifunctional iminophosphorane (BIMP) organocatalyst, is described. The iminophosphorane moiety of the catalyst provides the required basicity to deprotonate the thiol nucleophile while the chiral scaffold and H-bond donor control facial selectivity. The reaction is broad in scope with respect to the thiol and benzimidazole reaction partners with the reaction proceeding in up to 98% yield and 96 : 4 er.
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