52089-32-4

Upstream product

• 917-64-6 methyl magnesium iodide 
• 34713-70-7 2-Phenylpropanal 
• 769-59-5 3-phenyl-butan-2-one 
• 2085-88-3 2-methyl-2-phenyloxirane 
• 75-16-1 methylmagnesium bromide 
• 4564-81-2 1-phenyl-1,2-dimethyloxirane 
• 74-83-9 methyl bromide 
• 917-54-4 methyllithium 
• 74-88-4 methyl iodide 
• 94616-84-9 dichloromethylcerium 
• 58577-62-1 optically inactive 2-acetoxy-3-phenyl-butane 
• 135-98-8 sec-Butylbenzene 
• 591-51-5 phenyllithium 
• 21490-63-1 2,3-trans-epoxybutane 

Downstream Products

• 42879-20-9 (2S,3S)-3-phenylbutan-2-yl acetate 
• 42879-20-9 (2S,3R)-3-phenylbutan-2-yl acetate 
• 78549-49-2 (2R,3R)-3-phenylbut-2-yl acetate 
• 768-00-3 (E)-2-phenyl-2-butene 
• 70303-18-3 α-2-phenyl-3,4,4-trimethylpentan-3-ol 
• 70303-18-3 β-2-phenyl-3,4,4-trimethylpentan-3-ol 
• 41478-30-2 α-2-phenyl-3,4-dimethylpentan-3-ol 
• 41478-30-2 β-2-phenyl-3,4-dimethylpentan-3-ol 
• 33484-95-6 α-2-phenyl-3-methylpentan-3-ol 

Relevant academic research and scientific papers

Cram selectivity in the reaction of 2-phenylpropanal with alkyllithium reagents: Myth and reality

The reaction of racemic 2-phenylpropanal with methyl- and n-butyllithium was studied in detail. Factors such as temperature, solvent, rate of addition, presence of salts, scale-up and source of reagents were carefully examined. Cram-selectivities of 90-94

A General Regioselective Synthesis of Alcohols by Cobalt-Catalyzed Hydrogenation of Epoxides

A straightforward methodology for the synthesis of anti-Markovnikov-type alcohols is presented. By using a specific cobalt triphos complex in the presence of Zn(OTf)2 as an additive, the hydrogenation of epoxides proceeds with high yields and selectivities. The described protocol shows a broad substrate scope, including multi-substituted internal and terminal epoxides, as well as a good functional-group tolerance. Various natural-product derivatives, including steroids, terpenoids, and sesquiterpenoids, gave access to the corresponding alcohols in moderate-to-excellent yields.

A monolith immobilised iridium Cp catalyst for hydrogen transfer reactions under flow conditions

An immobilised iridium hydrogen transfer catalyst has been developed for use in flow based processing by incorporation of a ligand into a porous polymeric monolithic flow reactor. The monolithic construct has been used for several redox reductions demonstrating excellent recyclability, good turnover numbers and high chemical stability giving negligible metal leaching over extended periods of use.

Dynamic kinetic asymmetric amination of alcohols: From a mixture of four isomers to diastereo- and enantiopure α-branched amines

The first dynamic kinetic asymmetric amination of alcohols via borrowing hydrogen methodology is presented. Under the cooperative catalysis by an iridium complex and a chiral phosphoric acid, α-branched alcohols that exist as a mixture of four isomers undergo racemization by two orthogonal mechanisms and are converted to diastereo- and enantiopure amines bearing adjacent stereocenters. The preparation of diastereo- and enantiopure 1,2-amino alcohols is also realized using this catalytic system.

Desaturation of alkylbenzenes by cytochrome P450BM3 (CYP102A1)

A study was conducted to investigate the desaturation of alkylbenezenes by cytochrome P450BM3 (CYP102A1). It was observed during the study that oxidation of alkylbenzenes with CYP102A1 involves a gamut of P450 activity types that are terminal, sub-terminal benzylic and aromatic hydroxylation; terminal and sub-terminal desaturation; and epoxidation of the olefins. It was also found that the desaturation of cumene by CYP102A1 is sensitive to α-deuteration and insensitive to β-deuteration. Intramolecular deuterium isotope study revealed that the first abstraction in the desaturation of valproic acid and ezlopitant by microsomal P450s take place from activated carbon atoms. The increased β-hydroxylation percentages show that the β-carbon lies closer to the ferryl oxygen in the KT5.

Analysis of an unprecedented mechanism for the catalytic hydrosilylation of carbonyl compounds

This work details an in-depth evaluation of an unprecedented mechanism for the hydrosilylation of carbonyl compounds catalyzed by (PPh3) 2Re(O)2I. The proposed mechanism involves addition of a silane Si-H bond across one of the rhenium-oxo bonds to form siloxyrhenium hydride intermediate 2 that reacts with a carbonyl substrate to generate siloxyrhenium alkoxide 4, which, in turn, affords the silyl ether product. Compelling evidence for the operation of this pathway includes the following: (a) isolation and structural characterization by X-ray diffraction of siloxyrhenium hydride intermediate 2, (b) demonstration of the catalytic competence of intermediate 2 in the hydrosilylation reaction, (c) 1H and 31P{1H} NMR and ESI-MS evidence for single-turnover conversion of 2 into 1, (d) observation of intermediate 2 in the working catalyst system, and (e) kinetic analysis of the catalytic hydrosilylation of carbonyl compounds by 1.

Solvolysis of benzyl alcohols and ethers in 1,2-diols and application to a deprotection of benzyl ether-type protecting groups

Some kinds of benzyl alcohols and ethers react with 1,2-diols, such as ethylene glycol and propylene glycol, at 130-190°C to give 2-hydroxyethyl or 2-hydroxypropyl ethers. Application of this reaction to a deprotection of benzyl ether-type protecting groups, under neutral conditions, was also described. Copyright

Grignard reactions in imidazolium ionic liquids

A new, base-stable, imidazolium room-temperature ionic liquid (RTIL) has been prepared and applied to the addition of Grignard reagents to carbonyl compounds. These reactions occur readily at ambient temperature to afford the alcohol products in good to excellent yield. The RTIL can be recycled and reused numerous times without any difficulty.

Asymmetric transesterification of secondary alcohols catalyzed by feruloyl esterase from Humicola insolens

A new asymmetric transesterification of secondary alcohols catalyzed by feruloyl esterase from Humicola insolens has been found. Although alcohols are not the natural substrates for this enzyme, a high R enantioselectivity was observed. Stereochemical studies showed that variations in substrate structure lead to strong variations in enantioselectivity. The highest enantioselectivities are obtained when the β-carbon of the secondary alcohol is tertiary or quaternary.

Diastereoselective reduction of alkenylboronic esters as a new method for controlling the stereochemistry of up to three adjacent centers in cyclic and acyclic molecules

(figure presented) cis-Boronates are readily available via a diastereoselective Pd-catalyzed reduction of tetrasubstituted alkenylboronic esters using H2. Applying the reaction conditions presented to unsaturated open-chain boronic esters allows the stereochemistry of up to three adjacent centers to be controlled.