60550-53-0

Upstream product

• 41162-19-0 dimethyl(2-oxo-4-phenylbutyl)phosphonate 
• 75-07-0 acetaldehyde 
• 244176-55-4 5-bromomethyl-3-(2'-phenethyl)-Δ2-isoxazoline 
• 104-53-0 3-phenyl-propionaldehyde 
• 24850-33-7 allyltributylstanane 
• 122124-41-8 1-phenylhex-4-yn-3-one 
• 103-63-9 1-phenyl-2-bromoethane 
• 83334-11-6 (Z)-6-phenyl-4-hydroxy-hex-2-ene 
• 33046-41-2 6-phenylhex-3-en-2-one 
• 202932-64-7 1-phenyl-5-hexen-3-one 
• 74-95-3 1,1-dibromomethane 
• 221467-50-1 (S)-dimethyl(phenyl)(3-phenyl-2-tosylamidopropanoyl)silane 
• 90365-18-7 N-(p-toluenesulfonyl)-L-phenylalanyl chloride 
• 221467-54-5 (2S,3R)-3--1-phenyl-2-tosylamido-5-hexen-3-ol 

Downstream Products

• 1334687-64-7 C₂₃H₃₆OSi 
• 874337-89-0 C₂₁H₂₇BrO₅ 

Relevant academic research and scientific papers

Silver oxide(I) promoted Conia-ene/radical cyclization for a straightforward access to furan derivatives

A novel access to fused furan cores using silver oxide(I) has been developed. Mechanistic investigations indicate the involvement of a Conia-ene reaction/radical cyclization for an expedient path to complex furan derivatives. The reaction is broad in scop

Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone

A reliable method for enone transposition has been developed with the help of silyl group masking. Enantio-switching, substituent shuffling, and Z-selectivity are the highlights of the method. The developed method was applied for the first total synthesis of peribysin D along with its structural revision. Formal synthesis of E-guggulsterone and E-volkendousin was also claimed using a short sequence.

Photocatalytic Stoichiometric Oxidant-Free Synthesis of Linear Unsaturated Ketones from 1,2-Disubstituted Cyclopropanols

A one-step catalytic oxidant-free synthesis of unsaturated ketones from 1,2-disubstituted cyclopropanols is reported. Previously for this transformation, only two- and three-step protocols have been developed. The reaction proceeds under irradiation with visible light in the presence of catalytic amounts of both an acridinium photocatalyst and a cobaloxime complex. 2-Aryl-substituted cyclopropanols react giving α,β-unsaturated ketones, while dehydrogenative ring opening of 2-alkyl-substituted substrates affords mixtures of α,β- and β,γ-enones. The reaction starts with one-electron oxidation of a cyclopropanol to cyclopropyloxy radical, presumably, by the photoexcited acridinium catalyst. We also found that Co(dmgBF 2) 2(MeCN) 2complex under an air atmosphere and irradiation with blue LEDs or upon heating can serve as a hydroxycyclopropane oxidant.

Silver-catalyzed carbon dioxide incorporation and rearrangement on propargylic derivatives

A silver/DBU catalyst system was developed for the effective synthesis of cyclic carbonate and oxazolidinone from the reaction of CO2 with propargylic alcohols and propargylic amines, respectively, in high yields under mild conditions. It was f

Difluoro-λ3-bromane-induced oxidative carbon-carbon bond-forming reactions: Ethanol as an electrophilic partner and alkynes as nucleophiles

Reported here for the first time are the oxidative couplings of alkynes and primary alcohols yielding conjugated enones. Although the BF3-catalyzed reaction of terminal alkynes with p-trifluoromethylphenyl(difluoro)-λ3-bromane results in the fluoro-λ3-bromanation of triple bonds to afford (E)-β-fluorovinyl-λ3-bromanes, reaction of an alkyne with the difluoro-λ3-bromane in the presence of an alcohol and BF3-Et2O affords directly conjugated enones in good yields. The reaction proceeds in a highly stereo- and regioselective manner under metal-free conditions. Interestingly, no formation of enones was detected, when difluoro-λ3-iodane p-CF3C6H4IF2 was used instead of the λ3-bromane. A mechanism involving a λ3-bromane-induced oxidation of an alcohol to an aldehyde, [2 + 2] cyclization with alkynes yielding 2H-oxetes, and finally the electrocyclic ring opening is discussed. Copyright

Carbon dioxide-mediated catalytic rearrangement of propargyl alcohols into α,β-unsaturated ketones

In the presence of a catalytic amount of a silver salt with DBU under a CO2 atmosphere, various tertiary and secondary propargyl alcohols were efficiently converted into the corresponding α,β-unsaturated carbonyl compounds in high yield. An iso

Design of chiral N-triflyl phosphoramide as a strong chiral Bronsted acid and its application to asymmetric Diels-Alder reaction

A highly reactive and acidic chiral Bronsted acid catalyst, chiral N-triflyl phosphoramide, was developed. Highly enantioselective Diels-Alder reaction of α,β-unsaturated ketone with silyloxydiene was demonstrated using this chiral Bronsted acid catalyst. Copyright

Dibromomethane as one-carbon source in organic synthesis: Microwave-accelerated α-methylenation of ketones with dibromomethane and diethylamine

The reactivity of aryl alkyl ketone with a preheated mixture of dibromomethane and diethylamine is poor and gives an α-methylenation product in very low yield even under refluxing condition. It can be accelerated dramatically by microwave irradiation. Under microwave condition, the cyclic 1,3-dicarbonyls, aryl alkyl ketones, heteroaryl alkyl ketones and acyclic benzyl ketone give α-methylenation products in modest to good yields.

A chemoselective reduction of alkynes to (E)-alkenes

The trans reduction of all types of alkynes to give (E)-olefins is achieved through a two-stage trans hydrosilylation and protodesilylation. Reaction of an alkyne and a silane with the ruthenium catalyst [Cp*Ru(MeCN)3]PF6 results in

Catalytic asymmetric allylations of achiral and chiral aldehydes via BINOL-Zr complex

The complex generated from BINOL, Zr(OtBu)4, and 4 ? MS in toluene-pivalonitrile is very effective for catalytic asymmetric allylation of aldehydes using allyltributyltin. The reactions of achiral aldehyde under these conditions are completed within 3 h using 10-20 mol% of the complex at -20°C. The ees of homoallylic alcohols can be enhanced up to 98% via the tandem asymmetric allylation-Oppenauer oxidations. The scope and limitations of these conditions for β-alkoxy aldehydes were extensively examined.