The Mukaiyama aldol reaction uses a catalytic Lewis acid (e.g. TiCl4) or base, and an aqueous work-up to convert an aldehyde and an E- or Z-enol silane to an anti- and/or syn-diastereomer 1,3-ketol. The aldehyde is activated for nucleophilic attack when it coordinates to the Lewis acid, releasing a chloride ion in the process. The chloride ion then attacks the enol silane, forming TMSCl and an enolate, which attacks the aldehyde to afford the 1,3-ketol. The stereochemical outcome is based on the substrates and conditions used.

• Reagents: Lewis Acid or Base (Stoichiometric, Substoichiometric, or Catalytic), Aqueous Work-Up
• Reactant: Aldehyde, Z-or E-Enol Silane (Aldeyhyde, Ketone, Ester, or Thioester Derived)
• Product: 1,3-Ketol
• Type of Reaction: Lewis Acid Catalyzed Aldol Addition of Enol Derivatives

Mechanism

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