19980-24-6

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 103-79-7 1-phenyl-acetone 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 114643-78-6 4-Benzyl-1-trimethylsilanyl-pyridinium; iodide 
• 108-93-0 cyclohexanol 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 98-86-2 acetophenone 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 111-87-5 octanol 

Downstream Products

• 19980-46-2 (Z)-α-Methylstyryl Acetate 
• 76355-25-4 3-phenyl-8-nonen-2-one 
• 79999-03-4 1,2,4-triphenyl-3-methylhexane-1,5-dione 
• 420-56-4 trimethylsilyl fluoride 
• 73334-39-1 C₁₂H₃₀N₃S⁽¹⁺⁾*C₉H₉O^(1-) 
• 1066-40-6 Trimethylsilanol 
• 25975-32-0 enol of phenyl acetone 
• 769-59-5 3-phenyl-butan-2-one 
• 79999-01-2 2,4-dimethyl-3,5,6-triphenylpyridine 
• 1798-60-3 (R)-1-hydroxy-1-phenyl-2-propanone 
• 53439-91-1 (S)-phenylacetylcarbinol 

Relevant academic research and scientific papers

2,4,6-TRI-t-BUTYLPHENYLLITHIUM AS A BASE-----KINETIC DEPROTONATION OF BENZYL METHYL KETONE

An extremely bulky lithium reagent, 2,4,6-tri-t-butylphenyllithium, was applied for deprotonation of benzyl methyl ketone to give the kinetic enol ether by "in situ" quenching with chlorotrimethylsilane as the major product indicating that the reagent serves as a hindered base.

Regio- and stereoselective synthesis of silyl enol ethers using a new base electrogenerated from hexamethyldisilazane

The hexamethyldisilazane magnesium salt, a new base readily electrogenerated in an undivided cell fitted with a sacrificial magnesium anode, using a normally equilibrating medium (DME/15% vol HMPA mixture), exhibited a surprising regioselectivity leading to the less highly substituted silyl enol ethers from unsymmetrical ketones. This regioselectivity was not temperature dependent, but was strongly dependent on the nature and proportions of the solvent/cosolvent mixture. Moreover, the reaction was different in pure NMP, and exclusively afforded, from 2-pentanone, the new silylated aldol (56% yield) which resulted from the condensation of the less highly substituted enolate with the ketone.

Highly stereoselective oxazaborolidinium ion catalyzed synthesis of (Z)-silyl enol ethers from alkyl aryl ketones and trimethylsilyldiazomethane

Highly stereoselective (Z)-silyl enol ethers were prepared from alkyl aryl ketones and trimethylsilyldiazomethane (TMSD) using an oxazaborolidinium ion catalyst. In addition, ring-expanded silyl enol ethers were successfully constructed from cyclic ketones. Their synthetic utilities were shown by sequential Mukaiyama aldol and [2 + 2]-cycloaddition reactions.

Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates: Asymmetric formal synthesis of (-)-metazocine

(Chemical Equation Presented) Dirhodium(II) tetrakis[N- tetrafluorophthaloyl-(S)-tert-leucinate], Rh2(S-TFPTTL)4, is an exceptionally efficient catalyst for enantioselective aminations of silyl enol ethers derived from acyclic ketone

A new method for the preparation of silyl enol ethers from carbonyl compounds and (trimenthylsily)diazomethane in a regiospecific and highly stereoselective manner

The reaction of lithium (trimethylsilyl)diazomethane with aldehydes and ketones has been investigated, and it has been found that quenching at low temperature with MeOH followed by addition of Rh2(OAc)4 gave silyl enol ethers in high yields. Quenching with other electrophiles (e.g., deuterium, MeI) gave terminal and substituted silyl enol ethers with complete control over regio- and stereochemistry. The mechanism of this novel process has been mapped out through a combination of deuterium labeling, ReactIR, and isolation of reaction intermediates. Copyright

Facile synthesis of silyl enol ethers by Mg-promoted coupling of aliphatic carbonyl compounds with trimethylsilyl chloride

Treatment of aliphatic carbonyl compounds with trimethylsilyl chloride with Mg turning for Grignard reaction without any pre-treatment in N,N- dimethylformamide at room temperature brought about highly facile, effective and stereoselective coupling to give the corresponding silyl enol ethers in good yields.

First synthesis of Se-(β-Oxoalkyl) selenothiophosphates

General synthesis of a new class of Se-(β-oxoalkyl) selenothiophosphates based on selenothiophosphorylation of silyl enol ethers with thioxophosphoraneselenyl bromide is described.

Stereoselective electrochemical synthesis of silyl enol ethers using a sacrificial magnesium anode

The 2-pyrrolidone magnesium salt electrogenerated in an undivided cell fitted with a sacrificial magnesium anode allowed the stereoselective synthesis of Z-silyl enol ethers upon deprotonation of enolizable ketones in the presence of a complexing agent. Keywords: Silyl enol ethers; Stereoselective synthesis; Electrogenerated bases; Sacrificial magnesium anode

Chemistry of oxaziridines. 14. Asymmetric oxidation of ketone enolates using enantiomerically pure (camphorylsulfonyl)oxaziridine

The reagent-controlled asymmetric oxidation of tri- and tetrasubstituted ketone enolate anions 4 and 8 by enantiomerically pure (camphorylsulfonyl)oxaziridine 2 has been investigated. The stereoselectivities for oxidation of trisubstituted enolates 4a-d are good to excellent, 60-95% ee, while those for tetrasubstituted enolates 4e and 8 are lower; i.e., 21-30% ee. Isolated chemical yields for both types of enolate anions are good to excellent. The sodium enolate anions of 4a-d, which could be oxidized at -78°C, gave both higher yields and stereoselectivities than the corresponding lithium or zinc enolates, which required warming to higher temperatures for complete oxidation. The presence of HMPA generally had a deleterious effect on the stereoinduction. However, for oxidation of (E)- and (Z)-4d the highest ee's were observed in the presence of this additive. Investigation of the stereoselective trends reveals that the enolate substitution pattern and the enolate solution structure are the most important stereocontrol elements. The role that the enolate geometry has in the stereoinduction is less clear although Z enolates seem to exhibit higher stereoselectivities than the E enolates. The results obtained in this study have been formulated into a mechanistic rational involving an SN2-type substitution of the enolate anion on oxaziridine 2 via an "open" transition state.

SILICA SUPPORTED TETRABUTYLAMMONIUM FLUORIDE AS A CATALYST FOR THE SILYLATION OF CARBONYL ABD HYDROXY COMPOUNDS WITH ETHYLTRIMETHYLSILYLACETATE

the use of silica supported tetrabutylammonium fluoride (TBAF-SiO2) as a non hygroscopic catalyst for silylating ketones and aldehydes with ethyltrimethylsilylacetate (ETSA) gives predominantly kinetic and Z silylenolethers at room temperature.TBAF-SiO2/ETSA is also useful in the silylation of alcohols.