24257-70-3

Upstream product

• 873-66-5 1-propenylbenzene 
• 64-19-7 acetic acid 
• 108-05-4 vinyl acetate 
• 88196-06-9 syn-1-phenylpropane-1,2-diol 
• 93-55-0 1-phenyl-propan-1-one 
• 1443215-57-3 3-oxo-3-phenylprop-1-en-2-yl acetate 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 19347-08-1 acetic acid 1-methyl-2-oxo-2-phenyl-ethyl ester 
• 23355-97-7 1-phenylpropylene oxide 
• 766-90-5 cis-1-phenyl-1-propylene 
• 186581-53-3 diazomethane 

Downstream Products

• 40421-52-1 (1RS,2SR)-1-phenylpropane-1,2-diol 

Relevant academic research and scientific papers

A simple synthetic route to enantiopure α-hydroxy ketone derivatives by asymmetric hydrogenation

High enantioselectivities (up to 99% ee) have been observed for the catalytic asymmetric hydrogenation of the α-ketone enol acetates. DuanPhos has been proved to be the most effective ligand for this reaction. The high yield and enantioselectivity of the asymmetric hydrogenation of the α-ketone enol acetates represents a feasible synthetic route to important pharmaceutical building blocks: α-hydroxy ketones. Copyright

Diastereoselectivity in the reduction of α-oxy- and α-amino-substituted acyclic ketones by polymethylhydrosiloxane

Diastereoselectivity in the reduction of α-alkoxy-, α-acyloxy-, and α-alkylamino-substituted ketones with polymethylhydrosiloxane (PMHS) in the presence of fluoride ion catalysis was investigated. High syn-selectivity was observed in the reduction of α-alkoxy, α-acyloxy, and α-dialkylamino ketones. Reduction of α-monoalkylamino ketone proceeded in anti-selective manner with moderate selectivity. The observed selectivity is explained based on Felkin-Anh and Cram-chelate models.

The synthesis of the anti-malarial natural product polysphorin and analogues using polymer-supported reagents and scavengers.

A general asymmetric route to both enantiomers of polysphorin has been developed. The route utilizes polymer-supported reagents, catalysts and scavengers to minimise the need for aqueous work-up and chromatography. This includes application of a method to scavenge 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and a "catch-and-release" procedure to extract the resultant diol following Sharpless asymmetric dihydroxylation. A novel enzymatic selective protection and investigations of a new asymmetric dihydroxylation using microencapsulated osmium tetroxide were also investigated during the course of this study.

The Role of Copper(II) Salts in the Oxidation of Aryl-substituted Alkenes by Peroxydisulphate Anion

The effect of copper(II) ions on the oxidation, in acetic acid, of aryl-substituted alkenes by peroxydisulphate anion has been investigated.In the presence of the metal ions an electron-transfer process operates akin to that identified in the oxidation of alkenes by other one-electron oxidants.It is suggested that the electron-transfer agent is copper(III) and that the resultant alkene radical-cation is converted into hydroxy acetates in good yield.S2O8(2-) alone decomposes more slowly to SO4(*-) which undergoes radical addition to the alkene leading ultimately to diacetates.The presence of sodium acetate in the system reduces considerably the conversion of alkene as a result, it is suggested, of competitive oxidation of the acetate anion.

Oxidation by Cobalt(III) Acetate. Part 10. Effects of Ring Substituents on the Product Distributions in the Oxidation of β-Methylstyrenes by Cobalt(III) Acetate in Acetic Acid

The oxidation of ring-substituted β-methylstyrenes by cobalt(III) acetate in acetic acid has been studied by product analysis and the relative rates were measured by a competition method.Electron-releasing groups (p-MeO, pMe and p-But) accelerated both the reaction rate and the formation of glycol monoacetates, while electron-withdrawing groups (p-Cl and m-Cl) not only retarded the reaction but also favoured the formation of allylic acetate instead of glycol monoacetate.The good relationship of relative rates with ?+ in the Hammett plot showed that both products were derived from the same intermediate.The reaction mechanism is discussed in connection with the stabilities of radical cations formed by a one-electron transfer from the olefins to cobalt(III) acetate.

Mechanisms for Manganese(III) Osidations with Alkenes

In the reaction of manganese(III) acetate with carboxylic acids and alkenes, three distinct processes have been identified which involve the alkene and two processes which are independent of alkene.A combination of product studies, rearrangements, dilution experiments and literature kinetic data allow the proposal of a unified mechanistic picture to describe these processes.Specifically, the role of α-H acidity of the carboxylyic acid component, electron deficient radical additions, metal complexed organic radicals, and the importance of an oxo-centered manganese(III) triangle are discussed as they relate to the lactone annulation reaction.Single electron transfer oxidation of alkenes is described as a route toward 1,2-diacetates of alkenes within the 8.1-7.5 eV I.P. range.Three less common modes of Mn(III) reaction are discussed and compared with the two primary processes of lactone annulation and 1,2-diacetate formation.

Manganese(III)-Mediated γ-Lactone Annulation

The annulation of a γ-lactone ring onto an alkene by manganese(III) acetate oxidation of acetic acid was investigated.The regioselectivity of addition to unsymmetrically substituted alkenes is reported along with the stereoselectivity of addition to various acyclic and cyclic alkenes.Alkenes with ionization potentials above 8.2 eV were found to react in good yield.The role of acetic anhydride in these reactions was studied, and it was shown to be oxidized faster than acetic acid and also led to different products.The fate of oxidized acetic acid or anhydridein the absence of suitable acceptor molecule has also been quantitatively identified.The relationship of enolizability, or C-H acidity, of the carboxylic acid being oxidized was established quantitatively.

OXIDATION BY COBALT(III) ACETATE. PART 6. A NOVEL SYNTHESIS OF THE GLYCOL MONOACETATES FROM AROMATIC OLEFINS IN WET ACETIC ACID

Oxidation of various aryl-conjugated olefins with cobalt(III) acetate in wet acetic acid under nitrogen affords the glycol monoacetates in moderate to good yields.None of the phenyl rearrangement product is formed in the present reactions.These results are best interpreted by assuming the formation of a Co-co-ordinated intermediate.