ArticleAdvanced science (Weinheim, Baden-Wurttemberg, Germany)2024
Construction of 1,3-Nonadjacent Stereogenic Centers Through Enantioselective Addition of α-Thioacetamides to α-Substituted Vinyl Sulfones Catalyzed by Chiral Strong Brønsted Base.
Article in Advanced science (Weinheim, Baden-Wurttemberg, Germany), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Catalytic Enantioselective Multicomponent Reactions of Sulfoxonium Ylides Enabled by a Formal Rearrangement-A Versatile Entry to Enantioenriched α-Sulfanyl Carbonyl Compounds.Angewandte Chemie (International ed. in English) · 2026Article
- Electrochemical Hofmann Rearrangement for Modular Synthesis of Unsymmetrical Ureas and Late-Stage Modification of Drugs.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Enantioselective Organocatalytic Addition of 1,3-Dicarbonyl Compounds to β-Arylvinyl Triflones.Organic letters · 2025Article
- Construction of 1,3-Nonadjacent Stereogenic Centers Through Enantioselective Addition of α-Thioacetamides to α-Substituted Vinyl Sulfones Catalyzed by Chiral Strong Brønsted Base.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
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4 authors.
Funding
Abstract
An enantioselective addition reaction for the construction of 1,3-nonadjacent stereogenic centers is developed by means of a chiral strong Brønsted base catalyst. The chiral sodium ureate catalyst efficiently promoted the reaction of α-thioacetamides as less acidic pronucleophiles with vinyl sulfones having a variety of α-substituents including aryl, alkyl and halo groups, and α-phenylacrylates, accomplishing the construction of various 1,3-nonadjacent stereogenic centers in highly diastereo- and enantioselective manners. This is a rare example of the construction of 1,3-nonadjacent stereogenic centers with less acidic pronucleophiles. In addition, the application of Michael acceptors having various types of α-substituents in a single catalyst system is achieved for the first time, demonstrating the utility of the present catalyst system for the construction of 1,3-nonadjacent stereogenic centers.
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