ArticleJournal of the American Chemical Society2022
Bifunctional Iminophosphorane-Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α,β-Unsaturated Amides.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 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
- Bifunctional Iminophosphorane Superbases Enable the Highly Enantioselective Sulfa-Michael Addition to Fully Substituted Cyclopropene Carboxylic Acid Derivatives.Journal of the American Chemical Society · 2025Article
- Broadly Applicable Copper(I)-Catalyzed Alkyne Semihydrogenation and Hydrogenation of α,β-Unsaturated Amides Enabled by Bifunctional Iminopyridine Ligands.Journal of the American Chemical Society · 2025Article
- Enantioselective Organocatalytic Addition of 1,3-Dicarbonyl Compounds to β-Arylvinyl Triflones.Organic letters · 2025Article
- Computational Identification of Potential Organocatalysts (CIPOC) Reveals a 2-aminoDMAP/Urea Catalyst Superior to Its Thiourea Analogue.Journal of the American Chemical Society · 2025Article
- Enantiocontrolled Cyclization to Form Chiral 7- and 8-Membered Rings Unified by the Same Catalyst Operating with Different Mechanisms.Journal of the American Chemical Society · 2025Article
- Efficient and Sustainable Electrosynthesis ofJACS Au · 2024Article
- Bicarbonate-binding catalysis for the enantioselective desymmetrization of keto sulfonium salts.Nature communications · 2024Article
- Article
- 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
- How the Chalcogen Atom Size Dictates the Hydrogen-Bond Donor Capability of Carboxamides, Thioamides, and Selenoamides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
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Authors and funding
5 authors.
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No grant is acknowledged in the PubMed record.
Abstract
The first metal-free catalytic intermolecular enantioselective Michael addition to unactivated α,β-unsaturated amides is described. Consistently high enantiomeric excesses and yields were obtained over a wide range of alkyl thiol pronucleophiles and electrophiles under mild reaction conditions, enabled by a novel squaramide-based bifunctional iminophosphorane catalyst. Low catalyst loadings (2.0 mol %) were achieved on a decagram scale, demonstrating the scalability of the reaction. Computational analysis revealed the origin of the high enantiofacial selectivity via analysis of relevant transition structures and provided substantial support for specific noncovalent activation of the carbonyl group of the α,β-unsaturated amide by the catalyst.
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