Related Experiment Video
Updated: May 9, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
The impact of the Mukaiyama aldol reaction in total synthesis
S B Jennifer Kan1, Kenneth K-H Ng, Ian Paterson
1Laboratory of Synthetic Organic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
Abstract:
Four decades since Mukaiyama's first reports on the successful application of silicon and boron enolates in directed aldol reactions, the ability of this highly controlled carbon-carbon bond-forming method to simultaneously define stereochemistry, introduce complexity, and construct the carbon skeleton with a characteristic 1,3-oxygenation pattern has made it a powerful tool for natural product synthesis. This Minireview highlights a number of representative total syntheses that demonstrate the impact of the Mukaiyama aldol reaction and discusses the underlying mechanistic rationale that determines the stereochemical outcomes.
More Related Videos
Related Concept Videos
Aldol Condensation with β-Diesters: Knoevenagel Condensation
C–C Bond Formation: Aldol Condensation Overview
Base-Catalyzed Aldol Addition Reaction
Acid-Catalyzed Aldol Addition Reaction
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
C–C Bond Cleavage: Retro-Aldol Reaction
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.

