In organic chemistry, the Mukaiyama aldol addition is an organic reaction and a type of aldol reaction between a silyl enol ether (R2C=CR−O−Si(CH3)3) and an aldehyde (R−CH=O) or formate (R−O−CH=O).[1] The reaction was discovered by Teruaki Mukaiyama in 1973.[2] His choice of reactants allows for a crossed aldol reaction between an aldehyde and a ketone (>C=O), or a different aldehyde without self-condensation of the aldehyde. For this reason the reaction is used extensively in organic synthesis.
^Mukaiyama, T.; Kobayashi, S. (1994). "Tin(II) Enolates in the Aldol, Michael, and Related Reactions". Org. React.46: 1. doi:10.1002/0471264180.or046.01. ISBN 0471264180.
^New aldol type reaction Teruaki Mukaiyama, Koichi Narasaka and Kazuo Banno Chemistry Letters Vol.2 (1973), No.9 pp. 1011–1014 doi:10.1246/cl.1973.1011
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The aldol reaction (aldoladdition) is a reaction in organic chemistry that combines two carbonyl compounds (e.g. aldehydes or ketones) to form a new β-hydroxy...
natural products and drugs such as Oseltamivir and Epothilone. Mukaiyamaaldoladdition Kohlpainter, Christian; Schulte, Markus; Falbe, Jürgen; Lappe,...
term aldol condensation is also commonly used, especially in biochemistry, to refer to just the first (addition) stage of the process—the aldol reaction...
as the Mukaiyamaaldol reaction. Published in 1973 as Mukaiyama was in the process of migrating to the University of Tokyo, it is a cross-aldol reaction...
carbon–carbon bond. Like the aldoladdition, the Michael reaction may proceed via an enol, silyl enol ether in the Mukaiyama–Michael addition, or more usually, enolate...
triflate is used in such reactions as aldol reactions and Diels–Alder reactions. An example is the Mukaiyamaaldoladdition reaction between benzaldehyde and...
enol ethers can also be used as masked enolate equivalents in the Mukaiyamaaldoladdition. Dehydration of metal chlorides with trimethylsilyl chloride in...
acylation, alkylation, esterification, dehydration, condensation, Mukaiyamaaldoladdition, and other reactions[citation needed] Other, less common uses for...
ethers are used in many reactions resulting in alkylation, e.g., Mukaiyamaaldoladdition, Michael reactions, and Lewis-acid-catalyzed reactions with SN1-reactive...
methods, the tail synthesis is by an original design. Teruaki Mukaiyama is an expert on aldol reactions and not surprisingly his Taxol version contains no...
oxidation. The conversion to alcohol 10 was accomplished via a Mukaiyamaaldoladdition using formaldehyde, iodonation to 11 (iodine, DMAP) was followed...
JAXA astronaut, Vice President Teruaki Mukaiyama, chemist, former professor, discoverer of Mukaiyamaaldoladdition Kensō Soai, chemist, professor, discoverer...
common reagents in organic synthesis as illustrated by the Mukaiyamaaldol reaction: In addition to the use of strong bases, enolates can be generated using...
1016/B978-0-08-052349-1.00027-5. ISBN 978-0-08-052349-1. Mukaiyama, T. (1982). "The Directed Aldol Reaction". Organic Reactions. Vol. 28. pp. 203–331. doi:10...
In particular, it catalyzes the Michael reaction and the Mukaiyamaaldol reaction. The addition of other metal iodides increases its catalytic activity...
synthesis Holton Taxol total synthesis Kuwajima Taxol total synthesis Mukaiyama Taxol total synthesis Wender Taxol total synthesis Nicolaou Taxol Synthesis...
a carbocupration/Mukaiyamaaldol reaction sequence (as shown in the figure above) carbocupration favors the formation of the Z-aldol. Yao, B.; Liu, Y...
preference for α,β-unsaturated compounds. The Mukaiyamaaldol reaction and the Sakurai reaction refer to the addition of silyl enol ethers and allylsilanes to...
an addition of the aldehyde unto the site originally containing an acidic β-proton in the ketone. He theorized the mechanism to be one of mixed-aldol; featuring...
common precursor as the intermediate, aldol adduct, is a crystalline solid. A chelation-controlled Mukaiyama-aldol reaction was used to set the stereogenicity...
7 was treated with magnesium bromide diisopropylamide and underwent an aldol reaction with 4-pentanal (8) to give β-hydroxyketone 9. The hydroxyl group...
triethylborane in toluene at -78 °C. Aldol reaction Blaise reaction Claisen condensation Example use in total synthesis: Mukaiyama Taxol total synthesis (B ring...
Lectureship Award 2012 Otto Bayer Award 2013 Horst-Pracejus-Preis 2013 Mukaiyama Award 2013 Ruhrpreis, Mülheim, Germany 2014 Cope Scholar Award, US 2014...
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