54322-88-2

Upstream product

• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 100-52-7 benzaldehyde 
• 92735-08-5 3-trimethylsiloxycyclohexene 
• 1125-88-8 benzaldehyde dimethyl acetal 

Relevant academic research and scientific papers

The Mukaiyama aldol and Mukaiyama-Michael reactions promoted by commercially available molecular sieves

The Mukaiyama aldol reaction of silyl ketene acetals with aldehydes has been effected by using commercially available 4 molecular sieves (4 MS) as a promoter. Various silyl ketene acetals and silyl enol ethers have been shown to be effective nucleophiles

Cationic iridium complex is a new and efficient Lewis acid catalyst for aldol and Mannich reactions

A cationic iridium complex [Ir(cod)2]SbF6 was found to be a new and efficient Lewis acid catalyst for Mukaiyama aldol and Mannich reactions. Aldehydes react smoothly with silyl enol ethers to give β-siloxy ketones in the presence of 0.5 mol % of [Ir(cod)2]SbF6. The reaction of N-alkyl arylaldimines with ketene silyl acetals in the presence of 5 mol % [Ir(cod)2]SbF6/P(OPh)3 gave β-amino esters. After Mannich reaction was complete, stirring of the reaction mixture for 24 h led to cyclization to give β-lactam. The reaction of N-aryl benzaldimine with silyl enol ether derived from acetophenone gave a tetrahydroquinoline derivative as a single diastereomer.

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).

Bismuth(III) Triflate: A Water-Stable Equivalent of Trimethylsilyl Triflate for the Catalysis of Mukaiyama Aldol Reactions

Bismuth tris-trifluoromethanesulfonate (1) has been found to be an efficient catalyst for the Mukaiyama aldol-type reactions.The catalytic activity of this catalyst is higher than the one previously reported for the rare earth triflates M(OTf)3 (M = Sc, L

Bismuth Trichloride as a New Efficient Catalyst in the Aldol Reaction and the Michael Reaction

In the presence of a catalytic amount of bismuth(III) trichloride (5 mol percent), silyl enol ethers react with aldehydes at room temperature in dichloromethane to give the corresponding aldols in good yields.Silyl enol ethers also have been found to reac

Crossed aldol-type reactions catalyzed by rhodium complexes

Crossed aldol-type reactions of enol trimethylsilyl ethers with aldehydes and ketones are smooth when carried out with a catalytic amount of a rhodium complex, Rh4(CO)12 or X (X=PF6 and ClO4; COD=cycloocta-1,5-diene, DPPB=1,4-bis(diphenylphosphino)butane), under neutral conditions.A suitable catalyst enables the isolation of three different types of aldol reaction product, β-trimethylsiloxy ketones, β-hydroxy ketones, and α,β-unsaturated ketones.Rh4(CO)12 and ClO4 also catalyze the reaction of enol trimethylsilyl ethers with acetals or ketals, whereas PF6 does not.When ClO4 is used as the catalyst, this type of aldol reaction is extended to the one-pot synthesis of trisubstituted furans from enol trimethylsilyl ether and α-trimethylsiloxy acetal.

BISMUTH TRICHLORIDE AS A NEW EFFICIENT CATALYST IN THE ALDOL REACTION

In the presence of a catalytic amount of bismuth trichloride (5 molpercent), silyl enol ethers react with aldehydes at room temperature to give the corresponding aldols in good yields.

New Application of Solid Acid to Carbon-Carbon Bond Formation Reactions: Clay Montmorillonite-Catalyzed Aldol Reactions of Silyl Enol Ethers with Aldehydes and Acetals

A new attempt of utilizing solid acid to the cross aldol reaction of silyl enol ethers with aldehydes or acetals has been investigated.Among solid acids employed, the reaction is promoted most effectively by a catalytic amount of aluminium ion-exchanged m

TRIMETHYLSILYL TRIFLATE CATALYZED ALDOL-TYPE REACTION OF ENOL SILYL ETHERS AND ACETALS OR RELATED COMPOUNDS

Trimethylsilyl triflate with or without added hindered tertiary amines catalyzes directed condensation of enol trimethylsilyl ethers with acetals, orthoformate, or 2-acetoxytetrahydrofuran or -pyrans to give the corresponding β-alkoxy carbonyl compounds.R

Electrogenerated Acid-Catalyzed Reactions of Acetals, Aldehydes, and Ketones with Organosilicon Compounds, Leading to Aldol Reactions, Allylations, Cyanations, and Hydride Additions

Exquisite use of electrogenerated acid (EG acid) in the silicon-mediated acid-catalyzed reactions; e.g., aldol reactions, allylations, cyanations, and hydride additions is described.The aldol reaction of acetals 1 with enol trimethylsilyl ethers 3 and 1,2-bis(trimethylsiloxy)alkenes 4 gives the corresponding adducts 5 and 6, respectively.The reaction proceeds smoothly with EG acid derived from perchlorate salts such as LiClO4, n-Bu4NClO4, and Mg(ClO4)2 in dichloromethane using platinum electrodes.The amount of electricity required to complete the reaction implies a cationic process which is mediated by the trimethylsilyl moiety.This aldol reaction is further developed with unprotected carbonyl compounds 2 with 3, giving the trimethylsilyl ethers of the adducts 7.Further utility of this EG acid as a catalyst for a chain reaction is exemplified by the successful application in the following conversions: (1) The allylation of acetals 1 with allyltrimethylsilane (8) to give 9, (2) the cyanation of acetals 1 and unmasked 2 with trimethylsilyl cyanide (10) to give 11, 12, and 13, and (3) the hydride addition of acetals 1 with triethylsilane (14) to give 15.