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

• 105618-99-3 1-(ethoxycarbonyl)-3-(methoxycarbonyl)-4-<2-(p-methoxyphenyl)-2-oxoethyl>-1,4-dihydropyridine 
• 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 
• 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 
• 54669-75-9 2-(p-methoxyphenacyl)-cyclohexanone 

Relevant academic research and scientific papers

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).

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.

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.

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.

[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