ArticleChemical science2017
Enantioselective bifunctional iminophosphorane catalyzed sulfa-Michael addition of alkyl thiols to unactivated β-substituted-α,β-unsaturated esters.
Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Implementing modular design principles for molecular homogeneous catalyst discovery.Catalysis science & technology · 2026Review
- 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
- Bifunctional Iminophosphorane Superbases Enable the Highly Enantioselective Sulfa-Michael Addition to Fully Substituted Cyclopropene Carboxylic Acid Derivatives.Journal of the American Chemical Society · 2025Article
- Synthesis of carbonyl-functionalized mercaptosilsesquioxane.Scientific reports · 2025Article
- Bicarbonate-binding catalysis for the enantioselective desymmetrization of keto sulfonium salts.Nature communications · 2024Article
- Catalytic Enantioselective Intramolecular Oxa-Michael Reaction to α,β-Unsaturated Esters and Amides.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
- Isothiourea-Catalyzed Enantioselective Michael Addition of Malonates to α,β-Unsaturated Aryl Esters.Organic letters · 2022Article
- Bifunctional Iminophosphorane-Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α,β-Unsaturated Amides.Journal of the American Chemical Society · 2022Article
- Phosphorus-Containing Superbases: Recent Progress in the Chemistry of Electron-Abundant Phosphines and Phosphazenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- BIMP-Catalyzed 1,3-Prototropic Shift for the Highly Enantioselective Synthesis of Conjugated Cyclohexenones.Angewandte Chemie (International ed. in English) · 2020Article
- A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst.Chemical science · 2020Article
- A Selenourea-Thiourea Brønsted Acid Catalyst Facilitates Asymmetric Conjugate Additions of Amines to α,β-Unsaturated Esters.Journal of the American Chemical Society · 2020Article
- Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters.Chemical science · 2019Article
- Phosphine Organocatalysis.Chemical reviews · 2018Review
- Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles.Chemical science · 2018Article
- Asymmetric Organocatalytic Sulfa-Michael Addition to Enone Diesters.The Journal of organic chemistry · 2018Article
- Enantio- and Diastereoselective Organocatalytic Conjugate Additions of Nitroalkanes to Enone Diesters.Organic letters · 2017Article
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3 authors.
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Abstract
The highly enantioselective sulfa-Michael addition of alkyl thiols to unactivated β-substituted-α,β-unsaturated esters catalyzed by a bifunctional iminophosphorane (BIMP) organocatalyst is described. The low acidity of the alkyl thiol pro-nucleophiles is overcome by the high Brønsted basicity of the catalyst and the chiral scaffold/thiourea hydrogen-bond donor moiety provides the required enantiofacial discrimination in the addition step. The reaction is broad in scope with respect to the alkyl thiol and β-substituent of the α,β-unsaturated ester, affords sulfa-Michael adducts in excellent yields (up to >99%) and enantioselectivity (up to 97 : 3 er) and can operate down to 1 mol% catalyst loading.
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