5773-41-1

Upstream product

• 563-80-4 3-methyl-butan-2-one 
• 100-52-7 benzaldehyde 
• 10596-47-1 4-(1-isopropyl-3-phenylprop-2-yn-1-yl)morpholine 
• 130901-66-5 dichloro-bis-(3-methyl-2-oxo-butyl)-λ⁴-tellane 
• 201230-82-2 carbon monoxide 
• 4515-80-4 dimethyltitanium diisopropoxide 
• 18006-13-8 methyltriisopropoxytitanium(IV) 
• 121077-68-7 (3-methyl-2-oxobutyl)triphenyl-arsonium bromide 
• 102-92-1 Cinnamoyl chloride 
• 920-39-8 isopropylmagnesium bromide 
• 345910-94-3 (E)-3-Phenyl-acrylic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester 
• 103-64-0 bromostyrene 
• 1888-75-1 isopropyllithium 
• 139313-56-7 4-methyl-1-phenyl-pent-1-yn-3-ol 

Downstream Products

• 69366-44-5 3-Hydroxy-3-isopropyl-5-phenyl-(E)-4-pentensaeure 
• 84175-54-2 (E)-5-Dimethylamino-4,4-dimethyl-1-phenyl-pent-1-en-3-one; hydrochloride 
• 86983-95-1 (1E)-4-methyl-1-phenylpent-1-en-3-ol 
• 5435-09-6 (4-methyl-3-oxo-1-phenyl-pentyl)-malonic acid diethyl ester 
• 187837-40-7 trans-(1R,2S)-1,2-epoxy-4-methyl-1-phenylpentan-3-one 
• 177314-50-0 trans-(1S,2R)-1,2-epoxy-4-methyl-1-phenylpentan-3-one 
• 111258-81-2 trans-(+/-)-2,3-Epoxy-1-isopropyl-3-phenylpropan-1-one 
• 69366-50-3 (E)-(4-methyl-3-methylenepent-1-en-1-yl)benzene 
• 220089-23-6 trans-(R)-4-methyl-1-phenyl-1-penten-3-ol 

Relevant academic research and scientific papers

Chemoselective reduction of ?,￠-unsaturated carbonyl and carboxylic compounds by hydrogen iodide

The selective reduction of ?,￠-unsaturated carbonyl compounds was achieved to produce saturated carbonyl compounds with aqueous HI solution. The introduction of an aryl group at an ? or ￠ position efficiently facilitated the reduction with good yield. The reaction was applicable to compounds bearing carboxylic acids and halogen atoms. Through the investigation of the reaction mechanism, it was found that Michael-type addition of iodide occurred to produce ￠-iodo compounds followed by the reduction of C-I bond via anionic and radical paths.

Decarboxylative Nazarov Cyclization-Based Chirality Transfer for Asymmetric Synthesis of 2-Cyclopentenones

Asymmetric synthesis of 2-cyclopentenones was achieved by chirality transfer based on Lewis acid catalyzed decarboxylative Nazarov cyclization of optically active cyclic enol carbonates, which are prepared by silver-catalyzed carbon dioxide incorporation into optically pure propargyl alcohols. The stereochemistry at the 4,5-positions of the 2-cyclopentenones was cleanly constructed by reflecting the stereochemistry of the starting materials. This method could be applied to various substrates to obtain the corresponding products in high yields with highly efficient chirality transfer.

Asymmetric transfer hydrogenation of cycloalkyl vinyl ketones to allylic alcohols catalyzed by ruthenium amido complexes

A chemoselective 1,2-reduction of cycloalkyl vinyl ketones via asymmetric transfer hydrogenation is described. The reduction proceeded smoothly with a chiral diamine ruthenium complex as a catalyst and a HCOOH-NEt3 azeotrope as both a hydrogen source and solvent under mild conditions. A wide range of 1-cycloalkyl chiral allylic alcohols were obtained in good yields and up to 87% ee. It was found that the alkyl group plays an important role in the enantioselectivity.

Stereospecific Decarboxylative Nazarov Cyclization Mediated by Carbon Dioxide for the Preparation of Highly Substituted 2-Cyclopentenones

Highly substituted 2-cyclopentenones were stereospecifically and regioselectively constructed with high catalytic efficiency through Lewis-acid catalyzed decarboxylative Nazarov cyclization of the cyclic carbonate derivative, which is prepared by reacting the propargyl alcohol with carbon dioxide in the presence of a silver catalyst. The stereochemistry of the 2-cyclopentenone is strictly controlled by the geometry of the alkene in the starting material. This method is applicable for various substrates.

Iridium-catalysed desilylative acylation of 1-alkenylsilanes

We report the iridium-catalysed desilylative acylation of styryl and dienyl silanes by acid anhydrides to afford (E)-α,β-unsaturated ketones. The [{Ir(μ-Cl)(cod)}2] catalyst is the first non-rhodium complex successfully applied for this type of

Helical-Peptide-Catalyzed Enantioselective Michael Addition Reactions and Their Mechanistic Insights

Helical peptide foldamer catalyzed Michael addition reactions of nitroalkane or dialkyl malonate to α,β-unsaturated ketones are reported along with the mechanistic considerations of the enantio-induction. A wide variety of α,β-unsaturated ketones, including β-aryl, β-alkyl enones, and cyclic enones, were found to be catalyzed by the helical peptide to give Michael adducts with high enantioselectivities (up to 99%). On the basis of X-ray crystallographic analysis and depsipeptide study, the amide protons, N(2)-H and N(3)-H, at the N terminus in the α-helical peptide catalyst were crucial for activating Michael donors, while the N-terminal primary amine activated Michael acceptors through the formation of iminium ion intermediates.

Electrophilic Cyanation of Boron Enolates: Efficient Access to Various β-Ketonitrile Derivatives

The highly efficient electrophilic cyanation of boron enolates using readily available cyanating reagents, N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) and p-toluenesulfonyl cyanide (TsCN), is reported. Various β-ketonitriles were prepared by this new protocol, which has a remarkably broad substrate scope compared to existing methods. The present method also allowed efficient synthesis of β-ketonitriles containing a quaternary α-carbon center. In addition, a preliminary result with the use of a chiral boron enolate for the enantioselective cyanation reaction is described.

Kinetic Resolution of Racemic Allylic Alcohols by Catalytic Asymmetric Substitution of the OH Group with Monosubstituted Hydrazines

A new strategy has been established for the kinetic resolution of racemic allylic alcohols through a palladium/sulfonyl-hydrazide-catalyzed asymmetric OH-substitution under mild conditions. In the presence of 1 mol % [Pd(allyl)Cl]2, 4 mol % (S)-SegPhos, and 10 mol % 2,5-dichlorobenzenesulfonyl hydrazide, a range of racemic allylic alcohols were smoothly resolved with selectivity factors of more than 400 through an asymmetric allylic alkylation of monosubstituted hydrazines under air at room temperature. Importantly, this kinetic resolution process provided various allylic alcohols and allylic hydrazine derivatives with high enantiopurity.

PROCESS FOR PRODUCING ALDEHYDES OR KETONES BY OXIDIZING ALCOHOLS WITH OXYGEN

Provided is a process for producing aldehydes or ketones by oxidizing alcohols with oxygen, which comprises oxidizing alcohols to aldehydes or ketones in an organic solvent at room temperature with oxygen or air as an oxidant, wherein ferric nitrate (Fe(NO3)3.9H2O), 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) and an inorganic chloride are used as catalysts, the reaction time is 1-24 hours, and the molar ratio of said alcohols, 2,2,6,6-tetramethylpiperidine N-oxyl and the inorganic chloride is 100:1?10:1?10:1?10. The present process has the advantages of high yield, mild reaction conditions, simple operation, convenient separation and purification, recoverable solvents, substrates used therefor being various and no pollution, and therefore it is adaptable to industrialization.

CuCl-catalyzed aerobic oxidation of allylic and propargylic alcohols to aldehydes or ketones with 1:1 combination of phenanthroline and bipyridine as the ligands

We developed a modified protocol for the oxidation of 2,3-allenyl alcohols using CuCl with 1:1 combination of phenanthroline and bipyridine as the catalyst. To further investigate the applicability of this system, other types of alcohols such as allylic and propargylic alcohols have been tested: we found that both allylic and propargylic alcohols may be oxidized to the corresponding aldehydes or ketones using molecular oxygen in air as the oxidant with moderate to excellent yields. Copyright