118627-07-9

Upstream product

• 108-22-5 Isopropenyl acetate 
• 5650-40-8 (S)-2-hydroxypropiophenone 
• 1443215-57-3 3-oxo-3-phenylprop-1-en-2-yl acetate 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 13266-91-6 (Z)-1-phenylprop-1-en-1-yl acetate 
• 64-19-7 acetic acid 
• 93-55-0 1-phenyl-propan-1-one 
• 132604-23-0 (R)-1-(2-Phenyl-[1,3]dithian-2-yl)-ethanol 
• 118535-77-6 (R)-1-[(E)-(S)-2-(1-Methoxy-1-methyl-ethyl)-pyrrolidin-1-ylimino]-1-phenyl-propan-2-ol 
• 118535-76-5 (R)-1-[(Z)-(S)-2-Methoxymethyl-pyrrolidin-1-ylimino]-1-phenyl-propan-2-ol 
• 118535-64-1 propiophenone (S)-1-amino-2-(1'-methoxy-1'-methylethyl)pyrrolidine hydrazone 
• 107538-61-4 (S)-(+)-2-(methoxymethyl)-1-(1-phenylpropylideneamino)pyrrolidine 
• 5650-40-8 2-hydroxypropiophenone 
• 70338-42-0 (E)-3,4-diphenylbut-3-en-2-ol 

Relevant academic research and scientific papers

Kinetic resolution of racemic α-hydroxy ketones by lipase-catalyzed irreversible transesterification

Asymmetric acetylation of racemic α-hydroxy ketones with isopropenyl acetate catalyzed by lipases afforded the optically active keto alcohols and acetates in high enantiomeric excess (up to 99%); an enzymatic kinetic resolution which may be performed on preparative scale.

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.

Expanding the Substrate Specificity of Thermoanaerobacter pseudoethanolicus Secondary Alcohol Dehydrogenase by a Dual Site Mutation

Here, we report the asymmetric reduction of selected phenyl-ring-containing ketones by various single- and dual-site mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). The further expansion of the size of the substrate binding pocket in the mutant W110A/I86A not only allowed the accommodation of substrates of the single mutants W110A and I86A within the expanded active site but also expanded the substrate range of the enzyme to ketones bearing two sterically demanding groups (bulky–bulky ketones), which are not substrates for the TeSADH single mutants. We also report the regio- and enantioselective reduction of diketones with W110A/I86A TeSADH and single TeSADH mutants. The double mutant exhibited dual stereopreference to generate the Prelog products most of the time and the anti-Prelog products in a few cases.

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

Chemoenzymatic dynamic kinetic resolution of allylic alcohols: A highly enantioselective route to acyloin acetates

Dynamic kinetic resolution (DKR) of a series of sterically hindered allylic alcohols has been conducted with Candida antarctica lipase B (CALB) and ruthenium catalyst 1. The optically pure allylic acetates obtained were subjected to oxidative cleavage to

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.

Enantioselective reductions of 2-acyl-1,3-dithianes using the corey oxazaborolidine catalyst

The enantioselective reduction of acyl dithianes has been achieved using the oxazaborolidine catalyst 1b. The dithiane group can then be hydrolyzed to the ketone or removed reductively.