7065-28-3

Upstream product

• 3277-89-2 phenethylmagnesium bromide 
• 78-95-5 chloroacetone 
• 75-18-3 dimethylsulfide 
• 2550-26-7 4-Phenyl-2-butanone 
• 6683-51-8 2-methyl-4-phenyl-1-butene 
• 1774-47-6 trimethylsulfoxonium iodide 
• 1003868-04-9 1-diazo-2-methyl-4-phenyl-1-(trimethylsilyl)butan-2-ol 
• 333-27-7 methyl trifluoromethanesulfonate 
• 2181-42-2 trimethylsulphonium iodide 
• 107535-38-6 1-iodo-2-methyl-4-phenyl-2-butanol 
• 100-44-7 benzyl chloride 

Downstream Products

• 40654-82-8 4-phenyl-2-methylbutanal 
• 130284-28-5 2-Methyl-2-phenethyl-pent-4-en-1-ol 
• 75074-59-8 4-phenyl-2-(hydroxymethyl)but-1-ene 
• 107535-38-6 1-iodo-2-methyl-4-phenyl-2-butanol 
• 103-05-9 4-phenyl-2-methyl-2-butanol 
• 41927-30-4 2-methyl-4-phenylbutan-1-ol 
• 113235-07-7 6-methyl-6-phenethyltetrahydropyran-2-one 
• 114807-01-1 2-methyl-2-(2-phenylethyl)thiirane 
• 2550-26-7 4-Phenyl-2-butanone 

Relevant academic research and scientific papers

SYSTEMS AND METHODS FOR REGIOSELECTIVE CARBONYLATION OF 2,2-DISUBSTITUTED EPOXIDES

Provided are methods of carbonylating cyclic substrates to produce carbonyl ated cyclic products. The cyclic substrates may be 2, 2-di substituted epoxides and the cyclic products may be β,β-di substituted lactones. The method may be carried out by forming and pressurizing a reaction mixture of the cyclic substrate, a solvent, carbon monoxide, and a [LA+][CO(CO)4-] catalyst, where [LA+] is a Lewis acid capable of coordinating to the cyclic substrate. The method may proceed with a regioselectivity of 90:10 or greater. The resulting carbonylated cyclic products may be converted to ketone aldol products that retain the stereochemistry and enantiomeric ratio of the carbonyl ated cyclic products.

Retro-Corey-Chaykovsky Epoxidation: Converting Geminal Disubstituted Epoxides to Ketones

Corey-Chaykovsky epoxidation has been widely applied in the conversion of aldehydes and ketones to epoxides with sulfonium and sulfoxonium ylides. The reverse transformation is realized for conversion of geminal disubstituted epoxides to ketones in the presence of DABCO in refluxing mesitylene. The method is a weak basic transformation from epoxides to ketones with loss of a methylene group and can be applied as an alternative strategy of the acid-catalyzed Meinwald rearrangement or oxidation for conversion of epoxides to carbonyl compounds.

Mild Iridium-Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β-Alkyl Amines

The isomerization of epoxides to aldehydes using the readily available Crabtree's reagent is described. The aldehydes were transformed into synthetically useful amines by a one-pot reductive amination using pyrrolidine as imine-formation catalyst. The reactions worked with low catalyst loadings in very mild conditions. The procedure is operationally simple and tolerates a wide range of functional groups. A DFT study of its mechanism is presented showing that the isomerization takes place via an iridium hydride mechanism with a low energy barrier, in agreement with the mild reaction conditions. (Figure presented.).

Facile synthesis of thietanes via ring expansion of thiiranes

Thietanes are pharmaceutically important cores of some biological compounds and intermediates of organic synthesis. Various thietanes were prepared from thiiranes via ring expansion through a reaction with trimethyloxosulfonium iodide in the presence of sodium hydride. The reaction process is a nucleophilic ring-opening reaction of thiiranes with dimethyloxosulfonium methylide, generated from trimethyloxosulfonium iodide and sodium hydride, and subsequent intramolecular displacement (cyclization) of thiolates to the dimethyloxosulfonium moiety. The current method provides a new strategy for efficient preparation of thietanes from readily available thiiranes.

Isomerization of terminal epoxides by a [Pd-H] catalyst: A combined experimental and theoretical mechanistic study

An unusual palladium hydride complex has been shown to be a competent catalyst in the isomerization of a variety of terminal and internal epoxides. The reaction displayed broad scope and synthetic utility. Experimental and theoretical evidence are provided for an unprecedented hydride mechanism characterized by two distinct enantio-determining steps. These results hold promise for the development of an enantioselective variant of the reaction.

Efficient catalytic Corey-Chaykovsky reactions involving ketone substrates

It has been demonstrated for the first time that a sulfide catalyst, utilised at 20 mol% loading, can promote methylene transfer to ketones in the presence of methyl triflate and an organic base. This metal-free methodology is of broad scope-both aliphatic and aromatic ketones (including trifluoromethyl ketones) can be converted to synthetically useful terminal epoxides in excellent yields at room temperature.

Resolution of 2,2-disubstituted epoxides via biocatalytic azidolysis

A practical procedure for the enzymatic resolution of 2-alkyl-2-aryl- disubstituted epoxides using the Codex HHDH P2E2 enzyme and sodium azide is reported. This method allowed the synthesis of novel regio-and enantioselective 1-azido-2-arylpropan-2-ols in

Facile two-step synthesis of 3-substituted indazoles using diazo(trimethylsilyl)methylmagnesium bromide

Diazo(trimethylsilyl)methylmagnesium bromide readily reacted with various ketones and aldehydes to give the corresponding 2-diazo-(2-trimethylsilyl) ethanols. These were efficiently converted to indazoles bearing hydroxymethyl units at the 3-position by intermolecular [3 + 2] cycloaddition with benzynes. The Royal Society of Chemistry 2009.

Facile synthesis of 1,1-disubstituted taurines

A series of 1,1 -disubstituted taurines was synthesized expeditiously from ketones via the Corey-Chaykovsky epoxidation with dimethylsulfonium methylide, episulfidation with potassium sulfocyanate, ring-opening reaction with ammonia in the presence of sil

Poly(ethylene glycol)-supported ααα-trifluoroacetophenone in dioxirane mediated alkene epoxidation reactions

Poly(ethylene glycol) (PEG) was used for the immobilization of ααα-trifluoroacetophenone and the utility of this supported ketone has been examined in dioxirane mediated epoxidation of alkenes. The PEG-ketone reagent was found to be an effective homogeneous catalyst for the epoxidation of a variety of alkenes in the presence of Oxone A? and was readily recovered from the reaction mixtures and reused.