ArticleNature communications2022
Stereodivergent synthesis of chiral succinimides via Rh-catalyzed asymmetric transfer hydrogenation.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 43 citations in OpenAlex.
- Cu-Catalyzed dynamic kinetic asymmetric allylation enabled enantioselective assembly of sterically congested triaryl tertiary alcohols.Nature communications · 2026Article
- Triple Asymmetric Transfer Hydrogenation of 2-Arylidene-1,3-Indandiones.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Catalytic enantioselective total synthesis of antitubercular agents (-)-bedaquiline and (-)-sudapyridine enabled by dynamic kinetic resolution-asymmetric transfer hydrogenation.Chemical science · 2025Article
- Catalytic Asymmetric Transfer Hydrogenation of β,γ-Unsaturated α-Diketones.Journal of the American Chemical Society · 2024Article
- Upcycling poly(succinates) with amines to N-substituted succinimides over succinimide anion-based ionic liquids.Nature communications · 2024Article
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
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Abstract
Chiral succinimide moieties are ubiquitous in biologically active natural products and pharmaceuticals. Until today, despite the great interest, little success has been made for stereodivergent synthesis of chiral succinimides. Here, we report a general and efficient method for accessing 3,4-disubstituted succinimides through a dynamic kinetic resolution strategy based on asymmetric transfer hydrogenation. The Rh catalyst system exhibit high activities, enantioselectivities, and diastereoselectivities (up to 2000 TON, up to >99% ee, and up to >99:1 dr). Products with syn- and anti-configuration are obtained separately by control of the reaction conditions. For the N-unprotected substrates, both the enol and the imide group can be reduced by control of reaction time and catalyst loading. In addition, the detailed reaction pathway and origin of stereoselectivity are elucidated by control experiments and theoretical calculations. This study offers a straightforward and stereodivergent approach to the valuable enantioenriched succinimides (all 4 stereoisomers) from cheap chemical feedstocks in a single reaction step.
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