Catalytic Enantioselective Friedel–Crafts Reactions of Arenes Enabled by Iranium/Irenium-Ion-Triggered Electrophilic Functionalization

Synlett, Journal Year: 2025, Volume and Issue: unknown

Published: April 14, 2025

Abstract The catalytic asymmetric Friedel–Crafts reactions of (hetero)arenes represent a cornerstone in synthetic chemistry due to their ability efficiently incorporate aromatic rings into complex molecular architectures. This account presents comprehensive overview recent advancements the enantioselective (hetero)arenes, with particular focus on that facilitate introduction multiple C–C bonds via iranium/irenium-ion-triggered electrophilic processes. We examine detail strategies and methodologies employed achieve stereoselective incorporation unsaturated bonds, highlighting construction diverse structural scaffolds. Additionally, this showcases broad range applications powerful transformation organic synthesis. 1 Introduction 2 Catalytic Enantioselective Reactions Thiiranium/Thiirenium Ions 2.1 Arylthiiranium/Arylthiirenium-Ion-Triggered 2.2 Trifluoromethylthiiranium/Trifluoromethylthiirenium-Ion-Triggered 3 Haliranium 3.1 Chloriranium-Ion-Triggered 3.2 Bromiranium-Ion-Triggered 3.3 Iodiranium-Ion-Triggered Asymmetric Oxidative Arylation Alkenes 4 Conclusion Outlook

Language: Английский

Enantioselective Synthesis of Axially Chiral Heterobiaryl N‐Cbz‐Protected Diamines via Organocatalytic Arylation of 5‐Aminoisoxazoles

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: June 8, 2024

Abstract An enantioselective arylation of isoxazoles with N‐Cbz‐protected azonaphthalenes is disclosed, affording a range axially chiral arylisoxazoles in good yields and excellent enantiocontrol by utilizing phosphoric acid. Cbz protecting group can be readily removed, resulting five‐six membered heterobiaryl amines bearing free amine maintaining enantiomeric purity.

Language: Английский

Catalytic Atroposelective Friedel-Crafts Alkylation to Access Axially Chiral C2-Arylindoles via Dynamic Kinetic Resolutions

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 13, 2024

An amine-catalyzed atroposelective FC alkylation of 2-arylindoles with α,β-unsaturated aldehydes via the DKR process has been developed. Various axially chiral were obtained in good yields high enantioselectivities.

Language: Английский