Bifunctional NHC-Catalyzed Asymmetric Intramolecular Conjugate Addition via Noncovalent Interaction

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 28, 2025

Herein, we report a novel squaramide containing chiral bifunctional N-heterocyclic carbene (NHC) and its utilization in developing asymmetric intramolecular conjugate addition involving noncovalent interaction. Via concomitant activation of both electrophilic nucleophilic centers substrates, the reaction proceeds through well-organized transition state, thereby affording products with up to 94% ee broad scope. The process is found be scalable. initial mechanistic study supports nature newly designed NHC.

Language: Английский

Asymmetric Synthesis of Benzofuranones with a C3 Quaternary Center via an Addition/Cyclization Cascade Using Noncovalent N-Heterocyclic Carbene Catalysis

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 3, 2024

An asymmetric addition/cyclization cascade of amidoesters and iminoquinones is developed using noncovalent N-heterocyclic carbene (NHC) catalysis. The process enables access to various functionalized benzofuranones with an all-carbon quaternary stereocenter high yields ee values. reaction displays a broad substrate scope. Via product modifications, enantioenriched synthesis biologically relevant spirocyclic lactones lactams achieved. Substrate activation via interaction NHC suggested for the process.

Language: Английский

N-Heterocyclic carbene (NHC) organocatalysis: from fundamentals to frontiers

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 18, 2024

This tutorial review provides an overview of various important structural features and reactivity modes NHCs delves deep into the recent advances in NHC-organocatalysis.

Language: Английский