Related Experiment Video
Updated: Mar 8, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Direct Catalytic Asymmetric Aldol Reaction of α-Alkylamides
Zijian Liu1, Toshifumi Takeuchi1, Roman Pluta1
1Institute of Microbial Chemistry (BIKAKEN), Tokyo , 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
Abstract:
A catalytic asymmetric aldol reaction directly employing amides as latent enolates has remained elusive because of the resistance of amides to enolization. A direct aldol reaction of α-alkylamides without any electron-withdrawing group harnessed by specific activation of 7-azaindoline amides under soft Lewis acid/Brønsted base cooperative catalysis is reported. Diastereo- and enantioselective coupling with ynals and aromatic aldehydes as well as divergent functional group interconversion of the amide provided expeditious access to a variety of aliphatic and aromatic chiral building blocks.
Related Concept Videos
Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction
Base-Catalyzed Aldol Addition Reaction
Acid-Catalyzed Aldol Addition Reaction
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Intramolecular Aldol Reaction
C–C Bond Formation: Aldol Condensation Overview

