Related Experiment Video
Updated: Jun 7, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Copper(I)-Catalyzed Asymmetric Nucleophilic Addition to Aldehydes with Skipped Enynes
Cheng Peng1, Tianle Wu1, Xueyan Yang2
1School of Pharmacy, Xi'an Jiaotong University, No. 76 Yanta West Road, Xi'an, Shaanxi 710061, China.
Abstract:
The development of sustainable and novel strategies for constructing complex chiral molecules with versatile transformation potential is a long-term pursuit in the chemistry community. We report a copper(I)-catalyzed enyne addition to aldehydes under proton-transfer conditions, unlike previous examples which were limited to the use of preformed reactive nucleophiles containing allylic heteroatoms or electron-withdrawing groups. This protocol provides an efficient platform for installing chiral allylic alcohol moieties with a broad substrate scope and high regio-, stereo-, and enantioselectivity.
Related Concept Videos
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Base-Catalyzed Aldol Addition Reaction
Acid-Catalyzed Aldol Addition Reaction
Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation
Aldehydes and Ketones with Amines: Enamine Formation Mechanism
α-Alkylation of Ketones via Enolate Ions

