Photoredox catalyzed three-component tandem cyclization of 1,5-dienes with α-keto acids and water to access pyrrolidinones
- 23 May 2025
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- Vol. 61 (52) , 9456-9459
Abstract
This article reports a synthesis of hydroxyacylation substituted pyrrolidinone derivatives through regioselective tandem cyclization reaction of 1,5-dienes with phenylglyoxylic acid and water under visible light irradiation. This protocol features mild reaction conditions using a 12 W blue LED as the light source and CH3CN/H2O (1 : 1) as the solvent at room temperature. Additionally, a range of pyrrolidinones bearing two chiral centers can be easily accessed by this strategy, with the yields up to 78%, which makes the protocol more appealing toward natural product and medicinal chemistry development.Keywords
Funding Information
- National Natural Science Foundation of China (21172200)
This publication has 44 references indexed in Scilit:
- Photocatalytic Regioselective Tandem Cyclization Protocol to Trifluoromethylated PyrrolidonesEuropean Journal of Organic Chemistry, 2024
- Visible‐Light‐Induced Regioselective Selenohydroxylation of Enamine Amides with Diaryl DiselenidesEuropean Journal of Organic Chemistry, 2024
- Iron(II)‐Catalyzed Cyanoalkylsulfonylation/Annulation Cascades toward Functionalized Sulfonylated Pyrrolidone AlkylnitrilesAdvanced Synthesis & Catalysis, 2023
- Metal‐Free and Mild Synthesis of 2,4‐DiarylquinolinesEuropean Journal of Organic Chemistry, 2023
- Copper(I)‐Catalyzed Regioselective Tandem Cyanoalkylative Cyclization of 1,5‐Dienes with Cyclobutanone Oxime EstersEuropean Journal of Organic Chemistry, 2022
- 1,2‐Aryl Migration Induced by Amide C−N Bond‐Formation: Reaction of Alkyl Aryl Ketones with Primary Amines Towards α,α‐Diaryl β,γ‐Unsaturated γ‐LactamsAngewandte Chemie International Edition, 2021
- Refactoring the Concise Biosynthetic Pathway of Cyanogramide Unveils Spirooxindole Formation Catalyzed by a P450 EnzymeAngewandte Chemie International Edition, 2020
- Metal‐Free Oxidative Decarboxylative Acylation/Ring Expansion of Vinylcyclobutanols with α‐Keto Acids by Visible Light Photoredox CatalysisChinese Journal of Chemistry, 2017
- Discovery of potent pyrrolidone-based HIV-1 protease inhibitors with enhanced drug-like propertiesBioorganic & Medicinal Chemistry Letters, 2004
- Three novel cyclic amides from Clausena lansiumPhytochemistry, 1988