Asymmetric Substitution at the Tetrasubstituted Chiral Carbon: Catalytic Ring-Opening Alkylation of Racemic 2,2-Disubstituted Aziridines with 3‑Substituted Oxindoles

A highly diastereo- and enantioselective ring-opening alkylation of racemic 2,2-disubstituted aziridines with 3-substituted oxindoles is achieved under the catalysis of a chiral 1,2,3-triazolium salt. This reaction represents a hitherto unknown, catalytic stereoselective carbon–carbon bond formation through direct substitution at the tetrasubstituted chiral carbon

Catalytic Asymmetric Ring Openings of Meso and Terminal Aziridines with Halides Mediated by Chiral 1,2,3-Triazolium Silicates

Catalytic asymmetric chloride and bromide ring openings of meso aziridines with trimethylsilyl halides have been developed using modular chiral 1,2,3-triazolium chlorides as catalysts. Control experiments suggest the reaction pathway involving hypervalent silicate ions as reactive intermediates. The application of this system to the efficient kinetic resolution of terminal aziridines is also reported

Independence from the Sequence of Single-Electron Transfer of Photoredox Process in Redox-Neutral Asymmetric Bond-Forming Reaction

A catalytic cycle initiated by the oxidative quenching of the excited photosensitizer (Ir*­(ppy)₃) is established for the enantioselective coupling between (<i>N</i>-arylamino)­methanes and (<i>N</i>-methanesulfonyl)­aldimines catalyzed by Ir-based photosensitizer and a chiral (arylamino)­phosphonium tetrakis­[3,5-bis­(trifluoromethyl)­phenyl]­borate under visible light irradiation. This achievement clearly demonstrates the insensitivity of this redox-neutral asymmetric reaction to the sequence of the key redox events involved in the synergistic catalysis

Correction to “Generation of Chiral Phosphonium Dialkyl Phosphite as a Highly Reactive <i>P</i>‑Nucleophile: Application to Asymmetric Hydrophosphonylation of Aldehydes”

Correction to “Generation of Chiral Phosphonium Dialkyl Phosphite as a Highly Reactive <i>P</i>‑Nucleophile: Application to Asymmetric Hydrophosphonylation of Aldehydes

Asymmetric Substitution at the Tetrasubstituted Chiral Carbon: Catalytic Ring-Opening Alkylation of Racemic 2,2-Disubstituted Aziridines with 3‑Substituted Oxindoles

A highly diastereo- and enantioselective ring-opening alkylation of racemic 2,2-disubstituted aziridines with 3-substituted oxindoles is achieved under the catalysis of a chiral 1,2,3-triazolium salt. This reaction represents a hitherto unknown, catalytic stereoselective carbon–carbon bond formation through direct substitution at the tetrasubstituted chiral carbon

Acridinium Betaine as a Single-Electron-Transfer Catalyst: Design and Application to Dimerization of Oxindoles

An intramolecular ion-pairing acridinium phenoxide possessing a redox-active component and a basic site within a single molecular framework is developed. The potential of the acridinium betaine as a chemical redox catalyst is demonstrated by its application to the homodimerization of 3-aryl oxindoles, which proceeds through proton-coupled electron-transfer pathway. Analysis of the kinetic profile has provided important clues to understand the reaction mechanism

Asymmetric Substitution at the Tetrasubstituted Chiral Carbon: Catalytic Ring-Opening Alkylation of Racemic 2,2-Disubstituted Aziridines with 3‑Substituted Oxindoles

A highly diastereo- and enantioselective ring-opening alkylation of racemic 2,2-disubstituted aziridines with 3-substituted oxindoles is achieved under the catalysis of a chiral 1,2,3-triazolium salt. This reaction represents a hitherto unknown, catalytic stereoselective carbon–carbon bond formation through direct substitution at the tetrasubstituted chiral carbon

Catalytic Asymmetric Ring Openings of Meso and Terminal Aziridines with Halides Mediated by Chiral 1,2,3-Triazolium Silicates

Catalytic asymmetric chloride and bromide ring openings of meso aziridines with trimethylsilyl halides have been developed using modular chiral 1,2,3-triazolium chlorides as catalysts. Control experiments suggest the reaction pathway involving hypervalent silicate ions as reactive intermediates. The application of this system to the efficient kinetic resolution of terminal aziridines is also reported

Correction to “Chiral 1,2,3-Triazoliums as New Cationic Organic Catalysts with Anion-Recognition Ability: Application to Asymmetric Alkylation of Oxindoles”

Correction to “Chiral 1,2,3-Triazoliums as New Cationic Organic Catalysts with Anion-Recognition Ability: Application to Asymmetric Alkylation of Oxindoles

Acridinium Betaine as a Single-Electron-Transfer Catalyst: Design and Application to Dimerization of Oxindoles

An intramolecular ion-pairing acridinium phenoxide possessing a redox-active component and a basic site within a single molecular framework is developed. The potential of the acridinium betaine as a chemical redox catalyst is demonstrated by its application to the homodimerization of 3-aryl oxindoles, which proceeds through proton-coupled electron-transfer pathway. Analysis of the kinetic profile has provided important clues to understand the reaction mechanism