1528-39-8

Upstream product

• 56051-24-2 1,2-epoxy-2-methyl-1-phenyl-butane 
• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 1865-29-8 2-phenyl-acrylic acid methyl ester 
• 855243-42-4 3-methyl-2-phenyl-butane-1,3-diol 
• 769-68-6 2-phenylbutanenitrile 
• 19757-53-0 2-methyl-1-phenyl-butane-1,2-diol 
• 938-87-4 2-methyl-1-phenyl-butan-1-one 
• 917-54-4 methyllithium 
• 90-27-7 2-Phenylbutyric acid 
• 75-03-6 ethyl iodide 
• 103-79-7 1-phenyl-acetone 
• 107-87-9 2-Pentanone 
• 74-85-1 ethene 

Downstream Products

• 101775-48-8 1-dimethylamino-4-phenyl-hexan-3-one 
• 104177-98-2 1-methyl-2-phenyl-butylamine 
• 4564-82-3 3-Phenyl-penten-2-ol 
• 15329-81-4 3-benzyl-3-phenylpentan-2-one 
• 73862-72-3 3-(4-Chloro-2-nitro-phenyl)-3-phenyl-pentan-2-one 
• 105183-84-4 (S)-3-phenyl-2-pentanone 
• 2114-29-6 (S)-1-phenylpropyl acetate 
• 4165-78-0 (Z)-(1-ethylpropenyl)benzene 
• 4165-86-0 (E)-(1-ethylpropenyl)benzene 
• 609815-73-8 selenophosphoric acid O,O-diethyl ester Se-(1-ethyl-2-oxo-1-phenylpropyl) ester 
• 120625-81-2 C₁₈H₁₈N₄O₆ 
• 33484-98-9 3-Chlor-3-methyl-4-phenylhexan 
• 4564-82-3 erythro-3-phenylpentan-2-ol 
• 4564-82-3 threo-3-phenylpentan-2-ol 

Relevant academic research and scientific papers

Generation and Application of (Diborylmethyl)zinc(II) Species: Access to Enantioenriched gem-Diborylalkanes by an Asymmetric Allylic Substitution

We report the successful generation of (diborylmethyl)zinc(II) species by transmetallation beteween isolable (diborylmethyl)lithium and zinc(II) halide (X=Br, Cl) and their application in the synthesis of enantioenriched gem-diborylalkanes bearing a stereogenic center at the β-position of the diboryl groups by an asymmetric allylic substitution reaction. The reaction has a broad substrate scope, and various enantioenriched gem-diborylalkanes can be obtained in good yields with excellent enantioselectivity. Further elaboration of the enantioenriched gem-diborylalkanes provides access to a diverse set of valuable chiral building blocks.

Dynamic Reductive Kinetic Resolution of Benzyl Ketones using Alcohol Dehydrogenases and Anion Exchange Resins

Dynamic reductive kinetic resolutions of racemic 3-arylalkanones have been performed by the proper combination of an alcohol dehydrogenase and a basic anionic resin. The best results were found for the bioreduction with the alcohol dehydrogenase type A from Rhodococcus ruber DSM 44541 overexpressed in Escherichia coli (E. coli/ADH-A) and the commercially available evo-1.1.200, while the Amberlite IRA-440 C and the DOWEX-MWA-1 resins allowed efficient in situ racemizations. Reaction conditions were optimized in terms of enzyme source and loading, type and amount of resin, pH, temperature and reaction times, obtaining a series of (R,R)-substituted propan-2-ols with good conversions and both diastereoselectivity and stereoselectivity. As a proof of concept, the subsequent intramolecular cyclization of a selected propan-2-ol substrate afforded a valuable isochroman heterocycle without any loss of the optical purity.

Steric parameters in the Ir-catalyzed regio- and diastereoselective isomerization of primary allylic alcohols

The iridium-catalyzed diastereo- and regioselective isomerization of primary allylic alcohols using Crabtree's catalyst or sterically modified analogs is reported. The importance of the size of the substituents on either the substrates or the catalysts has been rationalized by linear free energy relationships.

Enzymatic kinetic resolution of racemic ketones catalyzed by Baeyer-Villiger monooxygenases

A set of racemic cyclic and linear ketones, as well as 2-phenylpropionaldehyde, were tested as substrates in the enzymatic Baeyer-Villiger oxidation catalyzed by two Baeyer-Villiger monooxygenases: phenylacetone monooxygenase (PAMO) and 4-hydroxyacetophenone monooxygenase (HAPMO). Excellent enantioselectivites (E > 200) can be obtained in the kinetic resolution processes depending on the substrate structure and the reaction conditions. The parameters affecting the biocatalytic properties of these enzymes were also studied, in order to establish a deeper understanding of these novel biocatalysts.

Dakin-West synthesis of β-aryl ketones

Triethylamine and 1-methylimidazole were found to be selective catalysts for the Dakin-West synthesis of diaryl ketones and aryl methyl ketones, respectively. In the 1-methylimidazole-catalyzed reaction, catalysis is due to the simultaneous formation of both an effective acylating agent, 1-acyl-3-methylimidazolium, and a base, carboxylate anion. Hydrocinnamic acid, a compound previously reported to be unreactive under Dakin-West conditions, forms 4-phenyl-2-butanone when the reaction is catalyzed by 1-methylimidazole.

Oxidative rearrangements of arylalkenes with [hydroxy(tosyloxy)iodo]benzene in 95% methanol: A general, regiospecific synthesis of α-aryl ketones

The treatment of arylalkenes with [hydroxy(tosyloxy)iodo]benzene in 95% methanol affords the corresponding α-aryl ketones. This oxidative rearrangement is general for acyclic and cyclic arylalkenes and permits regioselective syntheses of isomeric α-phenyl ketone pairs.

Synthesis of Enantiopure Homoallylic Ethers by Reagent Controlled Facial Selective Allylation of Chiral Ketones

The stereoselective allylation of chiral methyl ketones to give tertiary homoallylic ethers, which can easily be transformed into homoallylic alcohols, is described. Reaction of the enantiopure ketones 8a-d and the racemic ketones 26a-d with the norpseudoephedrine derivative 2 or ent-2 and allylsilane in the presence of a catalytic amount of trifluoromethanesulfonic acid, led to a series of homoallylic ethers with good to excellent diastereoselectivity (85:15 to > 97:3). The allylation is reagent controlled and nearly independent from the stereogenic centers in the substrates. A partial kinetic resolution was observed using the racemic ketones 26a-d. In the reaction of the chiral ketones 8a-d with the achiral reagents ethoxytrimethylsilane and allylsilane only a low diastereoselectivity was observed.

Synthesis and utility of α,α'-bis (triethyl ammonium methylene chloride) β-phenyl ethene in hydroxide ion initiated reactions - A new multi-site phase transfer catalyst

A three step synthesis of novel 'multi-site' water soluble phase transfer catalyst viz, α,α'-bis(triethyl ammonium methylene chloride) β-phenyl ethene and its utility in various organic biphase reactions are described.

Solid-Liquid Phase-Transfer Catalysis without Solvent: Selective Mono- and Di-alkylation of Benzyl Methyl Ketone

The alkylation of benzyl methyl ketone 1 has been performed by phase-transfer catalysis without solvent.Excellent yields of mono- 2 and di-alkyl derivatives 3 and 4 were obtained through general, selective and mild conditions.