5736-28-7

Upstream product

• 123-73-9 trans-Crotonaldehyde 
• 70-11-1 α-bromoacetophenone 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 121712-54-7 (2E,4E)-N-methoxy-N-methyl-hexa-2,4-dienamide 
• 109000-25-1 (E)-1-Phenyl-5-phenylselanyl-hex-2-en-1-one 
• 123873-45-0 6-phenyl-2,3-hexadienyl-6-one 
• 100-58-3 phenylmagnesium bromide 
• 110-44-1 sorbic Acid 
• 611-73-4 Benzoylformic acid 
• 3506-54-5 3-(diethylamino)-1-phenylprop-2-en-1-one 
• 13154-14-8 1-propenylmagnesium bromide 
• 123-73-9 crotonaldehyde 
• 3306-07-8 1-benzoyl-2-chloroethene 
• 98-86-2 acetophenone 

Downstream Products

• 58927-85-8 (3Z)-1-phenyl-3-hexen-1-ol 
• 58927-86-9 (E)-1-Phenyl-3-hexen-1-ol 
• 59321-58-3 1-Phenyl-4-hexen-1-ol 
• 57542-05-9 (E)-1-phenylhex-4-ene-1-one 
• 1354729-31-9 C₁₉H₂₂O 
• 1609386-46-0 1-phenyl-3-((E)-styryl)hex-4-en-1-one 
• 82706-91-0 (E)-1-Phenyl-hex-3-ene-1,5-dione 

Relevant academic research and scientific papers

Regio- and stereocontrol in the michael-initiated ring-closure reactions of γ,δ-epoxy-α,β-unsaturated esters, ketones, sulfones, and amides

Organozincates or Grignard reagents in the presence of zinc catalysts undergo Michael initiated ring closure (MIRC) reactions with γ,δ-epoxy-α,β-enoates, enones, enesulfones, and enamides to afford 1,2,3-trisubstituted cyclopropanes. The direction of dias

Enantioselective N -Alkylation of Nitroindoles under Phase-Transfer Catalysis

An asymmetric phase-transfer-catalyzed N -alkylation of substituted indoles with various Michael acceptors was studied. Acidities of nitroindoles were determined in acetonitrile by UV-Vis spectrophotometric titration. There was essentially no correlation between acidity and reactivity in the aza-Michael reaction. The position of the nitro group on the indole ring was essential to control the stereoselectivity of the reaction. Michael adducts were obtained in high yields and moderate enantioselectivities in the reaction between 4-nitroindole and various Michael acceptors in the presence of cinchona alkaloid based phase-transfer catalysts. In addition to outlining the scope and limitations of the method, the geometries of the transition states of the reaction were calculated.

Iron-facilitated oxidative radical decarboxylative cross-coupling between α-oxocarboxylic acids and acrylic acids: An approach to α,β-unsaturated carbonyls

The first Fe-facilitated decarboxylative cross-coupling reaction between α-oxocarboxylic acids and acrylic acids in aqueous solution has been developed. This transformation is characterized by its wide substrate scope and good functional group compatibility utilizing inexpensive and easily accessible reagents, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated carbonyls frequently found in bioactive compounds. The synthetic potential of the coupled products is also demonstrated in subsequent functionalization reactions. Preliminary mechanism studies suggest that a free radical pathway is involved in this process: the generation of an acyl radical from α-oxocarboxylic acid via the excision of carbon dioxide followed by the addition of an acyl radical to the α-position of the double bond in acrylic acid then delivers the α,β-unsaturated carbonyl adduct through the extrusion of another carbon dioxide.

Transition-Metal-Free Self-Hydrogen-Transferring Allylic Isomerization

Phenanthroline and tert-butoxide have been established as powerful radical initiators in reactions such as the SRN1-type coupling reactions due to the cooperation of large heteroarenes and a special feature of tert-butoxide. The first phenanthroline-tert-butoxide-catalyzed transition-metal-free allylic isomerization is described. The resulting ketones are key intermediates for indenes. The control experiments rule out the base-promoted allylic anion pathway. The radical pathway is supported by experimental evidence that includes kinetic study, kinetic isotope effect, isotope-labeling experiments, trapping experiments, and EPR experiments.

Enantioselective synthesis of allylboronates and allylic alcohols by copper-catalyzed 1,6-boration

Chiral secondary allylboronates are obtained in high enantioselectivities and 1,6:1,4 ratios by the copper-catalyzed 1,6-boration of electron-deficient dienes with bis(pinacolato)diboron (B2(pin)2). The reactions proceed efficiently using catalyst loadings as low as 0.0049 mol %. The allylboronates may be oxidized to the allylic alcohols, and can be used in stereoselective aldehyde allylborations. This process was applied to a concise synthesis of atorvastatin, in which the key 1,6-boration was performed using only a 0.02 mol % catalyst loading. 1,6-Borations of electron-deficient dienes with bis(pinacolato)diboron using copper catalyst loadings as low as 0.0049 mol % provided chiral allylboronates that, after oxidation, result in allylic alcohols in high enantioselectivities and 1,6:1,4 ratios. The allylboronates can also be used in stereoselective allylations of aldehydes. This process was applied to a concise synthesis of atorvastatin.

Stereoseleetive synthesis of polysubstituted alkenes through a phosphine-mediated three-component system of aldehydes, α-halo carbonyl compounds, and terminal alkenes

A study was conducted to demonstrate stereoselective synthesis of polysubstituted alkenes through a phosphine-mediated three-component system of aldehydes, α-halo carbonyl compounds, and terminal alkenes. Triphenylphosphine, α-halo carbonyl compounds, and methyl acrylate were added to a solution of aldehyde in chloroform or 1-propanol under nitrogen at room temperature. The resulting mixture was stirred at the specified temperature until transformation was completely observed by thin layer chromatography (TLC) analysis. The mixture was cooled to room temperature and purified by column chromatography on silica gel, eluting with petroleum ether/ethyl acetate. The study demonstrated that the first one-pot and three-component reaction of aldehydes, α-haloacetates, and terminal alkenes was developed in the presence of phenylphosphine to produce a wide range of trisubstituted alkenes with significant stereoselectivity.

1,5-Asymmetric induction of chirality: Highly diastereoselective addition reactions of organoaluminium reagents into ketone groups in the side-chain of π-allyltricarbonyliron lactone complexes

The utility of π-allyltricarbonyliron lactone complexes has been extended to include their use as chiral auxiliaries. Organoaluminium reagents add into ketone groups positioned in the side-chain of the allyl ligand to afford the corresponding tertiary alcohol complexes in good to excellent yield and with excellent diastereocontrol. Enantiomerically enriched complexes can be synthesised using the Sharpless asymmetric epoxidation protocol as the source of chirality. Addition products derived from endo ketones can be converted into the corresponding (E,E)-η4-dienetricarbonyliron complexes upon treatment with barium hydroxide solution without loss of diastereo- or enantio-purity.

Diastereoselective Addition Reactions to Carbonyl Groups in the Side-chain of ?-Allyltricarbonyliron Lactone Complexes

Organoaluminium reagents add in a highly diastereoselective fashion to carbonyl groups adjacent to the allyl system of ?-allyltricarbonyliron lactone complexes.

On tertiary stibine I. Reaction of ω-bromoacetophenone with aldehydes mediated by diphenylantimonyorganometallic reagents

In the presence of diphenylantimonymagnesium, various aldehydes react readily with ω-bromoacetophenone to form α,β-unsaturated ketones in good yields.