71268-59-2

Upstream product

• 557-91-5 1,1-Dibromoethane 
• 2078-12-8 trimethylsilyl benzoate 
• 5796-98-5 bis-trimethylsilanyl peroxide 
• 31076-47-8 [(1E)-1-bromoprop-1-en-1-yl]benzene 
• 38858-73-0 1-phenyl-1-trimethylsiloxycyclopropane 
• 75-77-4 chloro-trimethyl-silane 
• 93-55-0 1-phenyl-propan-1-one 
• 19917-00-1 trimethyl[(1-phenyl-2-propenyl)oxy]silane 
• 7449-74-3 N-methyl-N-trimethylsilylacetamide 
• 5908-41-8 benzoyltrimethylsilane 
• 6378-07-0 ethyl (p-tolyl)sulfoxide 
• 115262-00-5 [chloro(difluoro)methyl]trimethylsilane 
• 100-52-7 benzaldehyde 
• 51666-96-7 1-phenyl-2-(trimethylsilyl)-2-propen-1-ol 

Downstream Products

• 147766-14-1 (Z)/(E)-2-Brom-1-phenyl-1-(trimethylsiloxy)-1-propen 
• 95043-92-8 (2R,3S,4S)-4-(benzyloxy)-3-hydroxy-2-methyl-1-phenylpentan-1-one 
• 94233-76-8 (2S,3S,4S)-4-(benzyloxy)-3-hydroxy-2-methyl-1-phenylpentan-1-one 
• 76886-35-6 3-(benzyloxy)-2-methyl-1-phenylpropan-1-one 
• 96633-37-3 1-phenyl-2,3,3-trimethyl-5-p-tolyl-1,5-pentanedione 
• 61878-73-7 3-hydroxy-2-methyl-1,3-diphenyl-propan-1-one 
• 133225-48-6 anti-(2RS,3RS)-1,3-Diphenyl-2-methyl-3-<(trimethylsilyl)oxy>propan-1-one 
• 172907-58-3 1-(Dimethylamino)-3,4-dimethyl-2-phenyl-1H-pyrrole 
• 64274-26-6 4-methyl-N-(1-oxo-1-phenylpropan-2-yl)benzene sulfonamide 
• 743-93-1 1,3-Diphenyl-2-methyl-3-(N-phenyl)amino-1-propanone 
• 105824-16-6 2-methyl-1,3-diphenyl-pent-4-en-1-one 
• 253431-47-9 3-hydroxy-1,4-diphenyl-2-methylbutanone 
• 79314-55-9 3-hydroxy-2-methyl-1-phenylpentan-1-one 
• 28403-86-3 1-phenyl-2-(phenylthio)propan-1-one 

Relevant academic research and scientific papers

Halogenative difluorohomologation of ketones

A method for the difluorohomologation of ketones accompanied by halogenation of a C-H bond is described. The reaction involves silylation, difluorocarbene addition using Me3SiCF2Br activated by a bromide ion, and halogenation of intermediate cyclopropanes with N-bromo- or N-iodosuccinimide. The whole process is performed without isolation of intermediates. The resulting α,α-difluoro-β-halo-substituted ketones can be readily converted into fluorine containing pyrazole derivatives and oxetanes.

METHOD FOR PRODUCING SILYLENOL ETHERS

The present invention provides a method for producing a silyl enol ether compound, which is convenient, has highly broad utility and places a low environmental load (less waste). The present invention relates to a method for producing silyl enol ether compound (3), including reacting ketone or aldehyde compound (1) with allylsilane compound (2) in the presence of a base and 0.00001 to 0.5 equivalents of an acid catalyst relative to ketone or aldehyde compound (1), wherein R1 is a hydrogen atom, an alkyl group, an aryl group or the like; R2 and R3 are each a hydrogen atom, a halogen atom, an alkyl group, an aryl group or the like; R1 and R3, R1 and R2, or R2 and R3 optionally form a ring, together with the carbon atom(s) bonded thereto; R4 , R5 and R6 are each a hydrogen atom, an alkyl group or the like; two of R4, R5 and R6 optionally form a ring; R7, R8, R9, R10 and R11 are each a hydrogen atom, an alkyl group or the like; two of R7, R8, R9, R10 and R11 optionally form a ring.

Reaction of acylsilanes with α-sulfinyl carbanions: Regioselective synthesis of silyl enol ethers

The reaction of acylsilanes with α-sulfinyl carbanions such as α-lithioalkyl sulfoxide is described. The reaction proceeds to give silyl enol ethers preferentially through the initial formation of the α-silyl alkoxide intermediates. In particular, the products derived from enolizable acylsilanes were the regio-defined silyl enol ethers that cannot be obtained by usual enolization of the corresponding unsymmetrical ketones with base.

Lithium hexamethyldisilazide-mediated enolizations: Influence of triethylamine on E/Z selectivities and enolate reactivities

Lithium hexamethyldisilazide (LiHMDS) in triethylamine (Et 3N)/toluene is shown to enolize acyclic ketones and esters rapidly and with high E/Z selectivity. Mechanistic studies reveal a dimer-based mechanism consistent with previous studies of

In situ generation of Mes2Mg as a non-nucleophilic carbon-centred base reagent for the efficient one-pot conversion of ketones to silyl enol ethers

Treatment of commercially available MesMgBr with 1,4-dioxane produces the key Mes2Mg reagent in situ which then mediates the deprotonation of ketones to deliver trimethylsilyl enol ethers, at readily accessible temperatures and without any nucleophilic addition, in an expedient and high yielding one-pot process. The Royal Society of Chemistry.

Di-tert-butylmagnesium as an atom-efficient, carbon-centred base reagent for the preparation of silyl enol ethers from ketones

Di-tert-butylmagnesium has been found to be a reactive, yet non-nucleophilic and non-reductive, carbon-centred base for the deprotonation of a series of ketones. This reagent demonstrates equally high reactivity when used as either the pre-formed reagent, or in a more accessible one-pot protocol from the parent Grignard reagent, and offers improved atom-efficiency over more traditionally employed bases. Georg Thieme Verlag Stuttgart.

Bismesitylmagnesium: A thermally stable and non-nucleophilic carbon-centred base reagent for the efficient preparation of silyl enol ethers

Bismesitylmagnesium has been established as an accessible, practical, convenient, and non-nucleophilic carbon-centred base reagent for efficient access to silyl enol ethers from a series of ketone substrates at readily utilisable temperatures. The Royal Society of Chemistry.

Diastereomer-differentiating photochemistry of β-arylbutyrophenones: Yang cyclization versus type II elimination

The diastereomers of ketones 2 and 3 are shown to exhibit distinct photochemical reactivities due to conformational preferences; while the anti isomers of 2 and 3 undergo efficient Yang cyclization in 75-90% yields with a remarkable diastereoselectivity (> 90%), the syn isomers predominantly undergo Norrish Type II elimination. The differences in the product profiles of the diastereomers are consistent with a mechanistic picture involving the formation of precursor diastereomeric triplet 1,4-biradicals in which the substituents at α and β-positions stabilize the cisoid (cyclization) or transoid (elimination) geometry. The fact that such a diastereomeric relationship does indeed ensue at the triplet-excited-state itself is demonstrated via the nanosecond laser-flash photolysis of model ketones 1. The diastereomeric discrimination in the product profiles observed for ketones 2 and 3 as well as in the triplet lifetimes observed for ketones 1 can both be mechanistically traced back to different conformational preferences of the ground-state diastereomeric ketones and the intermediary 1,4-biradicals. Additionally, it emerges from the present study that the syn and anti diastereomers of ketones 2 and 3 represent two extremes of a broad range of widely examined butyrophenones, which lead to varying degrees of Yang photocyclization depending on the alkyl substitution pattern.

Silazanes/catalytic bases: Mild, powerful and chemoselective agents for the preparation of enol silyl ethers from ketones and aldehydes

We have developed an efficient method for the preparation of enol silyl ethers using novel agents, silazanes together with NaH or DBU catalyst, wherein TMS and TBDMS groups were smoothly and chemoselectively introduced into ketones and aldehydes under mil

A stereoselective isomerization of allyl silyl ethers to (E)- Or (Z)-silyl enol ethers using cationic iridium complexes

A cationic indium complex, prepared via the hydrogenation of [Ir(cod)2]PF6-2PPr3 is found to be an excellent catalyst for the stereoselective isomerization of primary allyl silyl ethers to (E)-enol ethers and secondary all