84896-29-7

Upstream product

• 75-52-5 nitromethane 
• 17510-46-2 3,3-dimethyl-2-(trimethylsilyl)oxy-1-butene 
• 100-52-7 benzaldehyde 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 5469-26-1 1-Bromopinacolon 

Downstream Products

• 42052-52-8 1-hydroxy-4,4-dimethyl-1-phenylpentan-3-one 

Relevant academic research and scientific papers

One-pot enol silane formation-Mukaiyama aldol reactions: Crossed aldehyde-aldehyde coupling, thioester substrates, and reactions in ester solvents

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and a trialkylamine base promote both in situ enol silane/silyl ketene acetal formation and Mukaiyama aldol addition reactions between a variety of reaction partners in a single reaction flask. Isolation of the required enol silane or silyl ketene acetal is not necessary. For example, crossed aldol reactions between α-disubstituted aldehydes and non-enolizable aldehydes yield β-hydroxy aldehydes in good yield. In a related reaction, the common laboratory solvent ethyl acetate functions as both an enolate precursor and a green reaction solvent. When thioesters are employed as enolate precursors, high yields for additions to non-enolizable aldehydes are routinely observed.

Organosilicon Reducing Reagents for Stereoselective Formations of Silyl Enol Ethers from α-Halo Carbonyl Compounds

Salt-free stereoselective synthesis of silyl enol ethers was achieved by treating α-halo carbonyl compounds with 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-dihydropyrazine. In this reaction, easily removable trimethylsilyl halides and 2,3,5,6-tetramethylpyrazine were generated as the reaction byproducts. Due to the inertness of the reaction byproducts, we found a one-pot transformation of the in situ generated silyl enol ethers into various α-functionalized carbonyls by reaction with Togni-II reagent or aldehydes.

ScIII-Doped zeolites as new heterogeneous catalysts: mukaiyama aldol reaction

ScIII-doped solids based on zeolite materials have been investigated for the first time as catalysts in organic synthesis. Sc III-USY zeolite proved to be a novel and very efficient heterogeneous catalyst for the Mukaiyama aldol reaction. This easy-to-prepare catalyst exhibited wide scope and compatibility with functional groups and is very simple to use, easy to remove (by simple filtration), and is recyclable (up to three times without loss of activity).

Organotin perchlorates as gentle Lewis acid catalysts in Mukaiyama reaction

Organotin perchlorates catalyze Mukaiyama reaction of ketene silyl acetal in highly chemoselective but uncommon manners. The competition reaction between aldehyde and acetal leads to exclusive formation of the aldehyde aldols leaving the acetal counterpar

METAL SALT-PROMOTED ALDOL REACTION OF SILYL ENOL ETHERS WITH ALDEHYDES

Simple metal salts such as lithium perchlorate and zinc triflate effectively promote aldol condensation between silyl enol ethers and aldehydes or acetals in non-protic solvents to yield the O-protected aldols in good yields. A slight preference for the syn aldol is observed when a prochiral silyl enol ether reacts with benzaldehyde, a complete syn stereoselectivity being obtained only in the case of the hindered silyl enol ether 14. The method appears to be simple and competitive with other ones previously described.

Fluoride Ion Catalyzed Aldol Reaction between Enol Silyl Ethers and Carbonyl Compounds

A new aldol reaction effected by the reaction of enol trimethylsilyl ethers and a quarternary ammonium fluoride is reported.Under the influence of a catalytic amount of tetrabutylammonium fluoride at low temperatures, enol silyl ethers react with various aldehydes to give the corresponding aldol trimethylsilyl ethers in fair to good yields.The silyl group of these products can be smoothly removed under mild conditions.Ketones, epoxides, and esters do not serve as electrophiles in this reaction.The reaction proceeds in a regiospecific manner with respect to the enol silyl ethers; the reactions of two regioisomers of 2-methylcyclohexanone with benzaldehyde cleanly give the respective regioisomeric aldol products.The reaction of 4-tert-butyl-1-methyl-2-(trimethylsiloxy)cyclohexene proceeds exclusively by the axial attack of the electrophile, making a strong contrast with the related cases reported on this cyclohexanone system.The aldol addition of a ketone and an aldehyde can be performed without the isolation of the enol silyl ether of the ketone by effecting both the silylation of the ketone and the aldol reaction with the aid of a fluoride anion.The characteristic behavior of the enolate species in this reaction can be rationalized by considering a mobile equilibrium in which the combination of fluorotrimethylsilane and a quarternary ammonium enolate functions as key controlling factor.