84009-51-8

Upstream product

• 118-75-2 chloranil 
• 67-56-1 methanol 
• 1528-58-1 (E/Z)-3-phenyl-2-pentenoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 1067-74-9 Methyl diethylphosphonoacetate 
• 93-55-0 1-phenyl-propan-1-one 
• 15790-87-1 methyl 2-pentenoate 
• 98-80-6 phenylboronic acid 
• 5927-18-4 trimethyl phosphonoacetate 
• 925-90-6 ethylmagnesium bromide 
• 88738-78-7 bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 
• 87711-82-8 2-(Bis-methylsulfanyl-methylene)-1-phenyl-butan-1-ol 

Downstream Products

• 2880-06-0 (R)-(+)-methyl 3-phenylpentanoate 
• 16460-86-9 (S)-1,3-diphenylpentan-1-one 
• 1376710-87-0 (E)-N-methoxy-N-methyl-3-phenylpent-2-enamidee 
• 1528-58-1 (Z)-3-phenyl-2-pentenoic acid 
• 1528-58-1 (E)-3-phenyl-2-pentenoic acid 
• 84009-53-0 2,3-Diethyl-5-oxo-2,3-diphenyl-cyclopentanecarboxylic acid methyl ester 

Relevant academic research and scientific papers

Highly efficient synthesis of chiral aromatic ketones: Via Rh-catalyzed asymmetric hydrogenation of β,β-disubstituted enones

A succinct and efficient protocol was developed for the synthesis of chiral aromatic ketones via asymmetric hydrogenation of β,β-disubstituted enones with rhodium catalysts based on chiral bisphosphine thiourea ligands. A series of substrates (17 examples) was smoothly catalyzed to afford the corresponding chiral aromatic ketones in high conversions (>99%) with excellent enantioselectivities (up to 96% ee).

Addition reaction of arylboronic acids to aldehydes and α,β-unsaturated carbonyl compounds catalyzed by conventional palladium complexes in the presence of chloroform

Arylboronic acids react with aldehydes and α,β-unsaturated carbonyl compounds in the presence of a base and a catalytic amount of a palladium(0) complex with chloroform, affording the corresponding addition products in good yields, and chiral benzhydrol was obtained with up to 43% e.e. using (S,S)-bppm as a ligand. General palladium complexes have no catalytic activity without chloroform. Because chloroform is essential for this reaction, these reactions would be promoted by dichloromethylpalladium(II) species.

Direct competitive enzyme-linked immunosorbent assay for the determination of the highly polar short-chain sulfophenyl carboxylates

A direct enzyme-linked immunosorbent assay for the detection of the short-chain sulfophenylcarboxylic acids (SPCs), the main metabolites of the linear alkylbenzene-sulfonates, is reported. Six SPCs (2C3, 2C 4, 3C4, 2C

(E)-Selective Horner-Wadsworth-Emmons reaction of aryl alkyl ketones with bis(2,2,2-trifluoroethyl)phosphonoacetic acid

The stereoselective Horner-Wadsworth-Emmons reaction of aryl alkyl ketones with bis(2,2,2-trifluoroethyl)phosphonoacetic acid utilizing lithium hexamethyldisilazide in DMF afforded (E)-α,β-unsaturated carboxylic acids as the major products.

Stereoselective synthesis of tetrasubstituted (Z)-alkenes from aryl alkyl ketones utilizing the Horner-Wadsworth-Emmons reaction

Tetrasubstituted (Z)-alkenes were readily prepared through the Horner-Wadsworth-Emmons reactions of methyl 2-[bis(2,2,2-trifluoroethyl) phosphono]propionate with aryl alkyl ketones by employing Sn(OSO 2CF3)2 and N-ethylpiperidine.

Stereoselective synthesis of 3-alkylcinnamic esters via coupling reaction of (2Z)-3-(aryltelluro) cinnamic esters in presence of CuI

Coupling reaction of (2Z)-3-(aryltelluro) cinnamic esters with Grignard reagents in presence of CuI produced trisubstituted alkenes containing ester groups with retention of configuration.

Stereoselective coupling reaction of (2Z)-β-arylselenocinnamic esters with Grignard reagents in presence of CuI

Stereoselective synthesis of trisubstituted alkenes linked with ester groups via coupling reaction of (2Z)-β-arylselenocinnamic esters with Grignard reagents in presence of Equal molar quantities of CuI was reported.

New reaction mode of the Horner-Wadsworth-Emmons reaction using Sn(OSO2CF3)2 and N-ethylpiperidine

Excellent Z or E selectivity is observed in the Horner-Wadsworth-Emmons reactions of methyl bis(trifluoroethyl)phosphonoacetate 2 with aryl alkyl ketones 3a-d or aldehydes 3f,g using Sn(OSO2CF3)2 in the presence of N-ethylpiperidine, which should have a different reaction mode to those using sodium hydride.

Electron Transfer Profile of Cyclopropanone Acetals in the Nonirradiated Reaction with Tetracyanoethylene, Chloranil, and Dicyanodichlorobenzoquinone

The donor profiles of cyclopropanone acetals 1 and 2 were examined in the reactions with electron acceptors (TCNE, DDQ, chloranil, and 1-cyanonaphthalene).With TCNE under nonirradiating conditions, an exclusive 2 + 2 cycloaddition took place stereospecifically with monosubstituted acetals 1a-c but nonstereospecifically with disubstituted acetals 1d,e.With quinones, a ring-opening of the cyclopropane and its coupling with the quinone took place to give the C (cyclopropane)-O (quinone) adduct 9 (with chloranil) or 10 (with DDQ), the latter of which underwent the elimination of a phenol to produce unsaturated esters 5 and 6.In addition, the intervention of the C (cyclopropane)-C (quinone) adduct 14 (with chloranil) or 15 (with DDQ), both as the precursor of 5 and 6, was also postulated.With 1-cyanonaphthalene, under photolysis, the cis/trans isomerization of 1 and 2 occured.The results provided evidences that cyclopropanone acetals, in general, are prone to function as donors.The mechanism of the reaction with quinones, in particular, was investigated in detail.

Formation of Unsaturated Esters in the Single Electron Transfer Reaction of Cyclopropanone Acetals with Quinones under Non-irradiated Conditions

Unsaturated esters were formed from cyclopropanone aceytals in the reaction with DDQ or chloranil, where ring-opened C-C and C-O bonded adducts were the intermediates formed via a SET mechanism resulting in the ester formation.