80676-78-4

Upstream product

• 77086-38-5 ketene t-butyldimethylsilyl methyl acetal 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 90720-43-7 4-Ethyl-1-(4-methoxy-phenyl)-hexane-1,3-dione 
• 90720-29-9 3-(tert-Butyl-dimethyl-silanyloxy)-2,2-diethyl-3-(4-methoxy-phenyl)-cyclobutanone 
• 90720-38-0 3-(tert-Butyl-dimethyl-silanyloxy)-4-ethyl-1-(4-methoxy-phenyl)-hex-3-en-1-one 
• 90720-37-9 3-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-phenyl)-4,4-diphenyl-but-3-en-1-one 
• 22303-36-2 N-(4-methoxyphenyl)-2-chloroacetamide 
• 105619-24-7 6,7-dichloro-1-(ethoxycarbonyl)-3-(methoxycarbonyl)-4-<2-oxo-2-(p-methoxyphenyl)ethyl>-1,4,4a,8a-tetrahydroquinoline 
• 1151770-63-6 (1S,2R)-methyl 1-(4-bromophenyl)-2-(tert-butyldimethylsilyloxy)-2-(4-methoxyphenyl)cyclopropanecarboxylate 
• 1151770-64-7 (1S,2S)-methyl 1-(4-bromophenyl)-2-(tert-butyldimethylsilyloxy)-2-(4-methoxyphenyl)cyclopropanecarboxylate 
• 768361-43-9 1-(4-methoxyphenyl)-2-(tert-butyldimethylsilanyloxy)ethanone 
• 4136-21-4 p-methoxybenzoylmethanol 
• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 

Relevant academic research and scientific papers

Copper-Catalyzed Fluoroolefination of Silyl Enol Ethers and Ketones toward the Synthesis of β-Fluoroenones

A general and facile synthetic method for β-fluoroenones from silyl enol ethers or ketones, with a copper-amine catalyst system, has been developed. The reaction proceeded by a tandem process of difluoroalkylation-hydrolysis-dehydrofluorination. This method is characterized by high yields, excellent Z/E ratios, a low-cost catalyst, and a broad substrate scope. The synthetic potential of β-fluoroenones has been demonstrated by the construction of various complicated organofluorine molecules.

FLP-Catalyzed Transfer Hydrogenation of Silyl Enol Ethers

Herein we report the first catalytic transfer hydrogenation of silyl enol ethers. This metal free approach employs tris(pentafluorophenyl)borane and 2,2,6,6-tetramethylpiperidine (TMP) as a commercially available FLP catalyst system and naturally occurring γ-terpinene as a dihydrogen surrogate. A variety of silyl enol ethers undergo efficient hydrogenation, with the reduced products isolated in excellent yields (29 examples, 82 % average yield).

Green organocatalytic α-hydroxylation of ketones

An efficient and green method for the α-hydroxylation of substituted ketones has been developed. This method includes the in situ conversion of various ketones into the corresponding silyl enol ethers and their oxidation to the corresponding α-hydroxy ketones. Two protocols have been established leading either to protected α-hydroxy carbonyls or free α-hydroxy ketones. Both procedures are easy to follow and lead to good to high yields for a variety of ketones.

The synthesis of pyrroles and oxazoles based on gold α-imino carbene complexes

Cationic gold complexes of α-oximimino carbenes have been identified to react with weak nucleophiles including enol ethers and nitriles. These findings allowed us to develop the highly efficient synthesis of pyrroles and oxazoles.

[4+2]-Annulations of aminocyclobutanes

The first [4 + 2]-annulation between aminocyclobutanes and aldehydes to access tetrahydropyranyl amines is reported. With phthalimido cyclobutane dicarboxylates and aromatic aldehydes, tetrahydropyrans were obtained in 53-92% yield and 3:1-17:1 dr using scandium triflate or iron trichloride as catalyst. The use of thymine-or fluorouracil-substituted cyclobutanes gave direct access to six-membered ring nucleoside analogues. Finally, the [4 + 2]-annulation between aminocyclobutanes and enol ethers led to the corresponding cyclohexylamines.

Intermolecular C-H functionalization versus cyclopropanation of electron rich 1,1-disubstituted and trisubstituted alkenes

Rhodium(II)-catalyzed reactions of aryldiazoacetates with electron rich 1,1-disubstituted and trisubstituted alkenes were systematically studied. The regio-, diastereo- and enantioselectivity of the chemistry was profoundly influenced by the nature of the

N-heterocyclic carbene-catalyzed silyl enol ether formation

N-Heterocyclic carbenes (NHCs) were found to catalyze the silyl transfer from trialkylsilyl ketene acetals to ketones. In the presence of a catalytic amount of NHC 3 (IAd, 0.1 to 5 mol%), a series of enolizable ketones as well as cyclohexanecarboxaldehyde