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The Mukaiyama aldol reaction: 40 years of continuous development.
Angew Chem Int Ed Engl. 2013 Aug 26; 52(35):9109-18.AC

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+Show Affiliations

Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kanazawa 920-1192, Japan. jimatsuo@p.kanazawa-u.ac.jpNo affiliation info available

Pub Type(s)

Journal Article
Review

Language

eng

PubMed ID

23881865

Citation

Matsuo, Jun-ichi, and Masahiro Murakami. "The Mukaiyama Aldol Reaction: 40 Years of Continuous Development." Angewandte Chemie (International Ed. in English), vol. 52, no. 35, 2013, pp. 9109-18.
Matsuo J, Murakami M. The Mukaiyama aldol reaction: 40 years of continuous development. Angew Chem Int Ed Engl. 2013;52(35):9109-18.
Matsuo, J., & Murakami, M. (2013). The Mukaiyama aldol reaction: 40 years of continuous development. Angewandte Chemie (International Ed. in English), 52(35), 9109-18. https://doi.org/10.1002/anie.201303192
Matsuo J, Murakami M. The Mukaiyama Aldol Reaction: 40 Years of Continuous Development. Angew Chem Int Ed Engl. 2013 Aug 26;52(35):9109-18. PubMed PMID: 23881865.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The Mukaiyama aldol reaction: 40 years of continuous development. AU - Matsuo,Jun-ichi, AU - Murakami,Masahiro, Y1 - 2013/07/23/ PY - 2013/04/16/received PY - 2013/7/25/entrez PY - 2013/7/25/pubmed PY - 2014/3/13/medline KW - aldol reaction KW - history of science KW - silyl enol ether KW - stereoselectivity KW - synthetic methods SP - 9109 EP - 18 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 52 IS - 35 N2 - 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. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/23881865/The_Mukaiyama_aldol_reaction:_40_years_of_continuous_development_ L2 - https://doi.org/10.1002/anie.201303192 DB - PRIME DP - Unbound Medicine ER -
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