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The Mukaiyama aldol addition is a Lewis acid-mediated addition of enol silanes to carbonyl (C=O) compounds. In this reaction, compounds with various organic groups can be used (see educts). [3] A basic version (R 2 = H) without the presence of chiral catalysts is shown below. Simplified overview with a stereocenter
The aldol reaction (aldol addition) is a reaction in organic chemistry that combines two carbonyl compounds (e.g. aldehydes or ketones) to form a new β-hydroxy carbonyl compound. Its simplest form might involve the nucleophilic addition of an enolized ketone to another:
A Mukaiyama aldol addition (magnesium bromide / toluene) took place between aldehyde 7 and ketene silyl acetal 8 with 71% stereoselectivity to alcohol 9 which was protected as the TBS ether 10 (TBSOTf, 2,6-lutidine). The ester group was reduced with DIBAL to an alcohol and then back oxidized to aldehyde 11 by Swern oxidation.
Silyl enol ethers are used in many reactions resulting in alkylation, e.g., Mukaiyama aldol addition, Michael reactions, and Lewis-acid-catalyzed reactions with S N 1-reactive electrophiles (e.g., tertiary, allylic, or benzylic alkyl halides).
The Mukaiyama aldol reaction and the Sakurai reaction refer to the addition of silyl enol ethers and allylsilanes to carbonyl compounds, respectively. Only under Lewis acid catalysis do these reactions occur under synthetically useful conditions.
Published in 1973 as Mukaiyama was in the process of migrating to the University of Tokyo, it is a cross-aldol reaction between a silyl enol ether (typically derived from a carbonyl of choice using the method of Stork [11]) and an aldehyde of choice in the presence of a Lewis acid like titanium(IV) chloride. The reaction is a landmark case on ...
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Pages in category "Addition reactions" The following 74 pages are in this category, out of 74 total. ... Mukaiyama aldol addition; Mukaiyama hydration; N. Nef ...