ArticleNature communications2019
Development of bifunctional organocatalysts and application to asymmetric total synthesis of naucleofficine I and II.
Article in Nature communications, 2019. 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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Who cites it
11 citing papers in PubMed.
- Bifunctional Catalysis of a Crossed Aldol Condensation by Diamines: Impact of Tether Composition and Length.The Journal of organic chemistry · 2026Article
- Asymmetric Mannich reaction enabled synthesis of alkaloids.Molecular diversity · 2026Review
- Direct Activation of Sulfides by C-H Oxidation with Photoexcited Nitroarenes: Formal Manipulations of the C─S Bond.Angewandte Chemie (International ed. in English) · 2025Article
- Recent advances in catalytic asymmetric synthesis.Frontiers in chemistry · 2024Review
- Recent Advances in Asymmetric Synthesis of Pyrrolidine-Based Organocatalysts and Their Application: A 15-Year Update.Molecules (Basel, Switzerland) · 2023Review
- Triflamides and Triflimides: Synthesis and Applications.Molecules (Basel, Switzerland) · 2022Review
- Cu(ii)/SPDO complex catalyzed asymmetric Baeyer-Villiger oxidation of 2-arylcyclobutanones and its application for the total synthesis of eupomatilones 5 and 6.Chemical science · 2022Article
- Rigid 3D-spiro chromanone as a crux for efficient antimicrobial agents: synthesis, biological and computational evaluation.RSC advances · 2021Article
- Enantioselective, Catalytic Multicomponent Synthesis of Homoallylic Amines Enabled by Hydrogen-Bonding and Dispersive Interactions.Journal of the American Chemical Society · 2021Article
- A modular and divergent approach to spirocyclic pyrrolidines.Chemical science · 2020Article
- H-bond donor-directed switching of diastereoselectivity in the Michael addition of α-azido ketones to nitroolefins.Chemical science · 2020Article
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Authors and funding
9 authors.
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Abstract
The proline-type organocatalysts has been efficiently employed to catalyze a wide range of asymmetric transformations; however, there are still many synthetically useful and challenging transformations that remain unachievable in an asymmetric fashion. Herein, a chiral bifunctional organocatalyst with a spirocyclic pyrrolidine backbone-derived containing fluoro-alkyl and aryl sulfonamide functionalities, are designed, prepared, and examined in the asymmetric Mannich/acylation/Wittig reaction sequence of 3,4-dihydro-β-carboline with acetaldehyde, acyl halides, and Wittig reagents. As a result, the spirocyclic pyrrolidine trifluoromethanesulfonamide catalyst can facilitate this versatile sequence as demonstrated by 18 examples displaying excellent enantioselectivity (up to 94% ee), as well as moderate to good yields (up to 54% over 3 steps). As a practical application, the asymmetric total synthesis of naucleofficine I (1a) and II (1b) in ten steps have been accomplished.
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