4528-19-2

Upstream product

• 4535-64-2 5-methyl-1-phenylhex-4-en-1-one 
• 98-86-2 acetophenone 
• 78-79-5 isoprene 
• 870-63-3 prenyl bromide 
• 2270-59-9 1-bromo-4-methylpent-3-ene 
• 100-52-7 benzaldehyde 
• 27644-03-7 4-methyl-1-phenyl-pent-3-en-1-ol 
• 36597-09-8 4-methyl-1-phenyl-3-penten-1-one 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 4535-59-5 ethyl 2-benzoyl-5-methylhex-4-enoate 
• 75-62-7 Bromotrichloromethane 
• 352200-57-8 N-(5-methyl-1-phenyl-4-hexen-1-oxy)-4-(p-chlorophenyl)-thiazole-2(3H)-thione 

Downstream Products

• 128797-89-7 1,5-dichloro-5-methyl-1-phenylhexane 
• 128797-91-1 2,5-trans-2-(1-acetoxy-1-methylethyl)-5-phenyltetrahydrofuran 
• 128797-92-2 2,5-trans-2-(1-hydroxy-1-methylethyl)-5-phenyltetrahydrofuran 
• 182144-04-3 1-(5-Methyl-1-phenyl-hex-4-enyloxy)-1H-pyridine-2-thione 
• 128797-92-2 2,5-cis-2-(1-hydroxy-1-methylethyl)-5-phenyltetrahydrofuran 
• 144121-61-9 (S)-5-methyl-1-phenyl-4-hexen-1-ol 
• 128797-93-3 (E)-2-methyl-6-phenylhex-4-en-3-one 
• 128797-94-4 (E)-2-methyl-6-phenylhex-5-en-3-one 

Relevant academic research and scientific papers

Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer

We report a catalytic, light-driven method for the intramolecular hydroetherification of unactivated alkenols to furnish cyclic ether products. These reactions occur under visible-light irradiation in the presence of an IrIII-based photoredox catalyst, a Br?nsted base catalyst, and a hydrogen-atom transfer (HAT) co-catalyst. Reactive alkoxy radicals are proposed as key intermediates, generated by direct homolytic activation of alcohol O?H bonds through a proton-coupled electron-transfer mechanism. This method exhibits a broad substrate scope and high functional-group tolerance, and it accommodates a diverse range of alkene substitution patterns. Results demonstrating the extension of this catalytic system to carboetherification reactions are also presented.

Stereoselective Synthesis of cis-2,5-Disubstituted Pyrrolidines via Copper-Catalyzed Cyclization of Alkenes

An efficient methodology for the stereoselective synthesis of cis-2,5-disubstituted pyrrolidines using copper catalyst was developed. The corresponding cis-2,5-disubstituted pyrrolidines could be obtained in reasonable yields and with good stereoselectivities in the presence of 4,4′-di-tert-butyl-2,2′-bipyridine as ligand and 1-methyl-2-pyrrolidinone as solvent.

Sodium amalgam mediated desulfonylative reduction of α-functionalized β-ketosulfones

Sodium amalgam mediated desulfonylative reduction of β-ketosulfones in MeOH at rt affords alcohols in good yields via radical desulfonylation of β-ketosulfones and sequential Bouveault-Blanc reduction of the resulting ketones.

Prins cyclization of α-bromoethers under basic conditions

α-Bromoethers have been found to undergo Prins-type cyclization under basic conditions and without the need to add a promoter. The products are those derived from a Markovnikov addition on the pendant alkene. However, the stereochemistry and even the structure of the products sometimes differ from those expected with the classical Lewis-acid-catalyzed Prins reaction of acetals.

Lithiated carbamates: Chiral carbenoids for iterative homologation of boranes and boronic esters

(Chemical Equation Presented) Take your pick: Either enantiomer of either diastereomer of substrates bearing adjacent stereogenic centers is accessible through reaction of an (R)- or (S)-lithiated carbamate with an (R)- or (S)-boronic ester (see scheme; pin = pinacolate, OCb = substituted carbamate).

Microwave-assisted generation of alkoxyl radicals and their use in additions, β-fragmentations, and remote functionalizations

Microwave irradiation (2.45 GHz, 300-500 W) of N-(alkoxy)thiazole-2(3H)- thiones in low-absorbing solvents affords alkoxyl radicals, which were identified by (i) spin adduct formation (EPR-spectroscopy) and (ii) fingerprint-type selectivities in intramolecular additions (stereoselective synthesis of disubstituted tetrahydrofurans), β-fragmentations (formation of carbonyl compounds), and C,H-activation of aliphatic subunits, by δ-selective hydrogen atom transfer. C-Radicals formed from oxygen-centered intermediates were trapped either by Bu3SnH, l-cysteine ethyl ester, the reduced form of glutathione (reductive trapping), or by bromine atom donor BrCCl3 (heteroatom functionalization) The results suggest that microwave activation is superior to UV/Vis-photolysis and conductive heating for alkoxyl radical generation from N-(alkoxy)thiazolethiones. It offers by far the shortest reaction times along with the option to reduce the amount of trapping reagent significantly. The Royal Society of Chemistry 2006.

HETEROCYCLISATIONS INDUCED BY THALLIUM(III) ACETATE. EFFECT OF VARYING THE INTERNAL NUCLEOPHILE

The stereochemistry of the 2,5-disubstituted tetrahydrofuran formed on treating 5-methyl-1-phenylhex-4-en-1-ol (6) with thallium(III) acetate in appropriate solvents has been established as trans by means of nuclear Overhauser experiments.Replacement of t