ArticleAngewandte Chemie (International ed. in English)2022
Catalytic Enantioselective Pictet-Spengler Reaction of α-Ketoamides Catalyzed by a Single H-Bond Donor Organocatalyst.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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11 citing papers in PubMed.
- Recent Progress in Catalytic Asymmetric Pictet-Spengler Reaction to Construct 1,1-Disubstituted Scaffolds.Synthesis · 2026Article
- Ynimines as versatile precursors to 2-imido- and 2-amido-1,3-dienes for stereodivergent diels-alder reactions.Nature communications · 2026Article
- Catalytic enantioselective synthesis of azahelicenes via cascade Pictet-Spengler reaction and dehydrogenative aromatization.Nature communications · 2026Article
- A Ketone-Accepting Pictet-Spenglerase for the Asymmetric Construction of 1,1-Disubstituted Tetrahydro-ß-carboline Alkaloids.Angewandte Chemie (International ed. in English) · 2025Article
- Divergent Enantioselective Total Synthesis of (-)-Ajmalicine, (+)-Mayumbine, and (-)-Roxburghine C.Organic letters · 2025Article
- Recent Advances in the Synthesis and Biological Activities of Quinolactacin and its Derivatives: A Comprehensive Review.Current organic synthesis · 2025Review
- Catalytic enantioselective nitrone cycloadditions enabling collective syntheses of indole alkaloids.Nature communications · 2024Article
- A genetic optimization strategy with generality in asymmetric organocatalysis as a primary target.Chemical science · 2024Article
- Enantioselective total syntheses of six natural and two proposed meroterpenoids fromChemical science · 2023Article
- A Catalytic Asymmetric Pictet-Spengler Platform as a Biomimetic Diversification Strategy toward Naturally Occurring Alkaloids.Journal of the American Chemical Society · 2022Article
- Catalytic Enantioselective Pictet-Spengler Reaction of α-Ketoamides Catalyzed by a Single H-Bond Donor Organocatalyst.Angewandte Chemie (International ed. in English) · 2022Article
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3 authors.
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Abstract
The asymmetric Pictet-Spengler reaction (PSR) with aldehydes is well known. However, PSR involving ketones as electrophilic partners is far-less developed. We report herein the first examples of catalytic enantioselective PSR of tryptamines with α-ketoamides. A new class of easily accessible prolyl-urea organocatalysts bearing a single H-bond donor function catalyzes the title reaction to afford 1,1-disubstituted tetrahydro-β-carbolines in excellent yields and enantioselectivities. The kinetic isotope effect using C2-deuterium-labelled tryptamine indicates that the rearomatization of the pentahydro-β-carbolinium ion intermediate might be the rate- and the enantioselectivity-determining step.
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