title: The impact of the Mukaiyama aldol reaction in total synthesis.
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.
authors.affiliation: Laboratory of Synthetic Organic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
authors.forename: S B Jennifer
authors.initials: SB
authors.lastname: Kan
authors.forename: Kenneth K-H
authors.initials: KK
authors.lastname: Ng
authors.forename: Ian
authors.initials: I
authors.lastname: Paterson
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000447:Aldehydes; D001688:Biological Products; C116609:3-hydroxybutanal
keywords: aldol reaction; enolates; natural products; polyketides; stereocontrol