Organocatalytic Atroposelective Synthesis of Axially Chiral Indolyl Ketosulfoxonium Ylides
Abstract: Despite recent advancements in the catalytic generation of axial chirality, reports on non‐biaryl atropisomers remain limited because of the stringent steric requirements necessary to establish effective rotational brakes. Herein, we present a novel class of monoaryl atropisomers, indolyl ketosulfoxonium ylides, and describe an organocatalytic protocol for their synthesis. We discovered that a chiral phosphoric acid (CPA) serves as an effective catalyst for the highly enantioselective iodination of ortho‐aminophenylethynyl sulfoxonium ylides. Under the optimized reaction conditions, a strong preference for the intended iodination process over the competing protonation was observed. Subsequently, intramolecular amide cyclization enabled the formation of sterically congested indole fragments. Furthermore, the synthetic utility of the products was demonstrated by showcasing versatile transformations into other chiral scaffolds with complete retention of optical purity.
- Location
-
Deutsche Nationalbibliothek Frankfurt am Main
- Extent
-
Online-Ressource
- Language
-
Englisch
- Bibliographic citation
-
Organocatalytic Atroposelective Synthesis of Axially Chiral Indolyl Ketosulfoxonium Ylides ; day:22 ; month:11 ; year:2024 ; extent:9
Angewandte Chemie / International edition. International edition ; (22.11.2024) (gesamt 9)
- Creator
-
Zhang, Ji‐Wei
Zhang, Yichi
Huang, Yong
- DOI
-
10.1002/anie.202413102
- URN
-
urn:nbn:de:101:1-2411231327313.238075057228
- Rights
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
-
15.08.2025, 7:26 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Zhang, Ji‐Wei
- Zhang, Yichi
- Huang, Yong
Other Objects (12)
Organocatalytic Atroposelective Synthesis of Axially Chiral Indolyl Ketosulfoxonium Ylides
Bibliometric analysis of GIS applications in heritage studies based on Web of Science from 1994 to 2023
A theory of emotion based on a universal model
Hypersurfaces of Prescribed k-Order Mean Curvature in Exterior Domains
Bending and free vibrational analysis of bi-directional functionally graded beams with circular cross-section
Lean blowout limits of a gas turbine combustor operated with aviation fuel and methane
Enantioselective Relay Coupling of Perfluoroalkyl and Vinylogous Ketyl Radicals
Enantioselective Relay Coupling of Perfluoroalkyl and Vinylogous Ketyl Radicals
A bootstrap based analysis pipeline for efficient classification of phylogenetically related animal miRNAs
Organocatalytic diastereo- and atroposelective construction of N–N axially chiral pyrroles and indoles
Gas Pool Coupled Activating TIG Welding Method with Coupling Arc Electrode
DMDP: A Dynamic Multi-source Default Probability Prediction Framework
Organocatalytic Atroposelective Synthesis of Axially Chiral Indolyl Ketosulfoxonium Ylides
Bibliometric analysis of GIS applications in heritage studies based on Web of Science from 1994 to 2023
A theory of emotion based on a universal model
Hypersurfaces of Prescribed k-Order Mean Curvature in Exterior Domains
Bending and free vibrational analysis of bi-directional functionally graded beams with circular cross-section
Lean blowout limits of a gas turbine combustor operated with aviation fuel and methane
Enantioselective Relay Coupling of Perfluoroalkyl and Vinylogous Ketyl Radicals
Enantioselective Relay Coupling of Perfluoroalkyl and Vinylogous Ketyl Radicals
A bootstrap based analysis pipeline for efficient classification of phylogenetically related animal miRNAs
Organocatalytic diastereo- and atroposelective construction of N–N axially chiral pyrroles and indoles
Gas Pool Coupled Activating TIG Welding Method with Coupling Arc Electrode
DMDP: A Dynamic Multi-source Default Probability Prediction Framework
Organocatalytic Atroposelective Synthesis of Axially Chiral Indolyl Ketosulfoxonium Ylides
Bibliometric analysis of GIS applications in heritage studies based on Web of Science from 1994 to 2023
A theory of emotion based on a universal model
Hypersurfaces of Prescribed k-Order Mean Curvature in Exterior Domains
Bending and free vibrational analysis of bi-directional functionally graded beams with circular cross-section
Lean blowout limits of a gas turbine combustor operated with aviation fuel and methane
Enantioselective Relay Coupling of Perfluoroalkyl and Vinylogous Ketyl Radicals
Enantioselective Relay Coupling of Perfluoroalkyl and Vinylogous Ketyl Radicals
A bootstrap based analysis pipeline for efficient classification of phylogenetically related animal miRNAs
Organocatalytic diastereo- and atroposelective construction of N–N axially chiral pyrroles and indoles
Gas Pool Coupled Activating TIG Welding Method with Coupling Arc Electrode