ArticleNature communications2019
Practical access to axially chiral sulfonamides and biaryl amino phenols via organocatalytic atroposelective N-alkylation.
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 17 papers.
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Who cites it
17 citing papers in PubMed.
- Atroposelective Synthesis of Azobenzenes by Palladium-Catalyzed Cross-Coupling of Racemic Biaryl Triflates and Diazenyl Pronucleophiles.Journal of the American Chemical Society · 2025Article
- Enantiopure Turbo Chirality Targets in Tri-Propeller Blades: Design, Asymmetric Synthesis, and Computational Analysis.Molecules (Basel, Switzerland) · 2025Article
- Recent advances in organocatalytic atroposelective reactions.Beilstein journal of organic chemistry · 2025Review
- Enantioconvergent and diastereoselective synthesis of atropisomeric hydrazides bearing a cyclic quaternary stereocenter through ternary catalysis.Chemical science · 2024Article
- Atroposelective catalysis.Nature reviews. Chemistry · 2024Review
- Asymmetric synthesis of P-stereogenic phosphindane oxides via kinetic resolution and their biological activity.Nature communications · 2024Article
- Article
- Cobalt-catalyzed enantioselective C-H/N-H annulation of aryl sulfonamides with allenes or alkynes: facile access to C-N axially chiral sultams.Chemical science · 2023Article
- Design and synthesis of axially chiral aryl-pyrroloindoles via the strategy of organocatalytic asymmetric (2 + 3) cyclization.Fundamental research · 2023Article
- Advances in the Asymmetric Synthesis of BINOL Derivatives.Molecules (Basel, Switzerland) · 2022Review
- Catalytic Enantioselective Synthesis of N-C Axially ChiralMolecules (Basel, Switzerland) · 2022Article
- Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C-N Axis via Enantioselective Catalysis.Molecules (Basel, Switzerland) · 2022Review
- Conformational enantiodiscrimination for asymmetric construction of atropisomers.Nature communications · 2022Article
- Stimuli Responsive Materials Supported by Orthogonal Hydrogen and Halogen Bonding or I···Alkene Interaction.Molecules (Basel, Switzerland) · 2021Article
- Atroposelective synthesis ofChemical science · 2021Article
- Insights on a new sulfonamide chalcone with potential antineoplastic application.Journal of molecular modeling · 2021Article
- Atropisomeric Properties ofThe Journal of organic chemistry · 2021Article
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8 authors.
Funding
Abstract
The importance of axial chirality in enantioselective synthesis has been widely recognized for decades. The practical access to certain structures such as biaryl amino phenols known as NOBINs in enantiopure form, however, still remains a challenge. In drug delivery, the incorporation of axially chiral molecules in systematic screening has also received a great deal of interest in recent years, which calls for innovation and practical synthesis of structurally different axially chiral entities. Herein we present an operationally simple catalytic N-alkylation of sulfonamides using commercially available chiral amine catalysts to deliver two important classes of axially chiral compounds: structurally diverse NOBIN analogs as well as axially chiral N-aryl sulfonamides in excellent enantiopurity. Structurally related chiral sulfonamide has shown great potential in drug molecules but enantioselective synthesis of them has never been accomplished before. The practical catalytic procedures of our methods also bode well for their wide application in enantioselective synthesis.
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