91111-01-2

Upstream product

• 36394-75-9 (S)-2-acetoxypropanoyl chloride 
• 71-43-2 benzene 
• 216099-55-7 (R,R)-1-(benzoyloxy)-1,2-epoxytetrahydronaphthalene 
• 13266-91-6 (Z)-1-phenylprop-1-en-1-yl acetate 
• 64-19-7 acetic acid 
• 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 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 6493-83-0 2-methoxy-1-phenyl-propan-1-one 
• 5650-40-8 2-hydroxypropiophenone 
• 535-17-1 (S)-2-acetoxypropionic acid 
• 19347-08-1 acetic acid 1-methyl-2-oxo-2-phenyl-ethyl ester 
• 216099-56-8 (S,R)-1-acetoxy-1-phenyl-1,2-epoxypropane 

Downstream Products

• 5650-40-8 2-hydroxypropiophenone 
• 19347-08-1 acetic acid 1-methyl-2-oxo-2-phenyl-ethyl ester 
• 88196-06-9 syn-1-phenylpropane-1,2-diol 
• 40421-52-1 (1RS,2SR)-1-phenylpropane-1,2-diol 
• 88196-06-9 (1S,2S)-1-phenyl-1,2-propanediol 
• 40421-52-1 (1R,2S)-1-phenylpropane-1,2-diol 
• 5650-40-8 (S)-2-hydroxypropiophenone 

Relevant academic research and scientific papers

Hypervalent Iodine(III)-Catalysed Enantioselective α-Acetoxylation of Ketones

An enantioselective catalytic synthesis of α-acetoxylated ketones through I(I)/I(III) catalysis using a resorcinol/lactamide-based chiral iodoarene is reported. Catalyst turnover by in situ generation of the active iodine(III) derivative is achieved by oxidation with mCPBA in the presence of acetic acid. The prior transformation of ketones to easily accessible acetyl enol ethers is beneficial and yields up to 97 percent with enantioselectivities up to 88 percent ee are obtained using only low catalyst loadings of only 5 mol percent under mild reaction conditions.

Asymmetric Oxidation of Enol Derivatives to α-Alkoxy Carbonyls Using Iminium Salt Catalysts: A Synthetic and Computational Study

We report herein the first examples of asymmetric oxidation of enol ether and ester substrates using iminium salt organocatalysis, affording moderate to excellent enantioselectivities of up to 98% ee for tetralone-derived substrates in the α-hydroxyketone products. A comprehensive density functional theory study was undertaken to interpret the competing diastereoisomeric transition states in this example in order to identify the origins of enantioselectivity. The calculations, performed at the B3LYP/6-31G(D) level of theory, gave good agreement with the experimental results, in terms of the magnitude of the effects under the specified reaction conditions, and in terms of the preferential formation of the (R)-enantiomer. Just one of the 30 characterized transition states dominates the enantioselectivity, which is attributed to the adoption of an orientation relative to stereochemical features of the chiral controlling element that combines a CH interaction between a CH2 group in the substrate and one of the aromatic rings of the biaryl section of the chiral auxiliary with a good alignment of the acetoxy group with the other biaryl ring, and places the smallest substituent on the alkene (a hydrogen atom) in the most sterically hindered position.

Palladium-Catalyzed Oxidative Synthesis of α-Acetoxylated Enones from Alkynes

We report a palladium-catalyzed oxidative functionalization of alkynes to generate α-acetoxylated enones in one step. A range of functional groups are well-tolerated in this reaction. Mechanistic studies, including the use of 18O-labeled DMSO,

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

NMR determination of absolute configuration of α-acyloxy ketones

Determination of the absolute configuration of several acyclic α-acyloxy-ketones, and δ-ketobutanolides, in the presence of a chiral solvating agent, by low temperature and low concentration 1H NMR analysis, is reported.

Simple chemoenzymatic access to enantiopure pharmacologically interesting (R)-2-hydroxypropiophenones

A chemoenzymatic synthesis of pharmacological interesting (R)-2-hydroxypropiophenones starting from propiophenone derivatives is described. Manganese(III) acetate-mediated acetoxylation followed by fungus-mediated hydrolysis of propiophenone derivatives affords (R)-2-hydroxypropiophenones in high enantiomeric excess.

Enantioselective synthesis and stereoselective rearrangements of enol ester epoxides

Enol esters can be epoxidized with high enantioselectivities using the fructose-derived chiral ketone 1 as catalyst and Oxone as oxidant. A detailed study of enantiomerically enriched enol ester epoxides has revealed that the acid-catalyzed rearrangement can proceed through two distinct pathways, one with retention of configuration and the other with inversion. The competition between the two pathways is highly dependent upon the nature of the acid catalyst. A strong acid favors retention of configuration and a weak acid favors inversion of configuration. Under thermal conditions, these epoxides rearrange highly stereoselectively with inversion of configuration. Either enantiomer of an α-acyloxy ketone can be formed from one enantiomer of an enol ester epoxide by judicious choice of reaction conditions.

A simple procedure for the synthesis of enantiopure α-acetoxy ketones

Cross-coupling reactions of α-acetoxy carboxylic acid chlorides with organocopper reagents, derived from Grignard reagents, cuprous bromide and lithium bromide, provide a simple and straightforward method for the synthesis of enantiopure α-acetoxy ketones.

Highly enantioselective epoxidation of enol silyl ethers and esters

High enantioselectivities have been obtained for asymmetric epoxidation of enol silyl ethers and esters using a fructose-derived chiral ketone as catalyst and Oxone as oxidant.