title: The Mukaiyama aldol reaction: 40 years of continuous development.
abstract: A directed cross-aldol reaction of silyl enol ethers with carbonyl compounds, such as aldehydes and ketones, promoted by a Lewis acid, a reaction which is now widely known as the Mukaiyama aldol reaction. It was first reported in 1973, and this year marks the 40th anniversary. The directed cross-aldol reactions mediated by boron enolates and tin(II) enolates also emerged from the Mukaiyama laboratory. These directed cross-aldol reactions have become invaluable tools for the construction of stereochemically complex molecules from two carbonyl compounds. This Minireview provides a succinct historical overview of their discoveries and the early stages of their development.
authors.affiliation: Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kanazawa 920-1192, Japan. jimatsuo@p.kanazawa-u.ac.jp
authors.forename: Jun-ichi
authors.initials: J
authors.lastname: Matsuo
authors.forename: Masahiro
authors.initials: M
authors.lastname: Murakami
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; history of science; silyl enol ether; stereoselectivity; synthetic methods