ArticleChemical science2023
Enantioselective isothiourea-catalysed reversible Michael addition of aryl esters to 2-benzylidene malononitriles.
Article in Chemical science, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- From Oxygen to Tellurium: The Impact of the Chalcogen on Nucleophilicities and Basicities of Isochalcogenourea Catalysts.Angewandte Chemie (International ed. in English) · 2025Article
- Determination of the pEuropean journal of organic chemistry · 2025Article
- Isothiourea - catalyzed α-selective glycosylations.Chemical communications (Cambridge, England) · 2025Article
- Isochalcogenourea-catalyzed asymmetric (4 + 2)-heterocycloadditions of allenoates.Chemistry letters · 2024Article
- Chiral Isochalcogenourea-Catalysed Enantioselective (4+2) Cycloadditions of Allenoates.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2024Article
- Chiral Isochalcogenourea-Catalysed Enantioselective (4+2) Cycloadditions of Allenoates.Angewandte Chemie (International ed. in English) · 2024Article
- Cooperative Chiral Lewis Base/Palladium-Catalyzed Asymmetric Syntheses of Methylene-Containing δ-Lactams.European journal of organic chemistry · 2023Article
- Chiral Lewis Base-Catalysed Asymmetric Syntheses of Benzo-fused ϵ-Lactones.European journal of organic chemistry · 2023Article
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7 authors.
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Abstract
Catalytic enantioselective transformations usually rely upon optimal enantioselectivity being observed in kinetically controlled reaction processes, with energy differences between diastereoisomeric transition state energies translating to stereoisomeric product ratios. Herein, stereoselectivity resulting from an unusual reversible Michael addition of an aryl ester to 2-benzylidene malononitrile electrophiles using an isothiourea as a Lewis base catalyst is demonstrated. Notably, the basicity of the aryloxide component and reactivity of the isothiourea Lewis base both affect the observed product selectivity, with control studies and crossover experiments indicating the feasibility of a constructive reversible Michael addition from the desired product. When this reversible addition is coupled with a crystallisation-induced diastereomer transformation (CIDT) it allows isolation of products in high yield and stereocontrol (14 examples, up to 95 : 5 dr and 99 : 1 er). Application of this process to gram scale, plus derivatisations to provide further useful products, is demonstrated.
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