146388-50-3

Upstream product

• 100-52-7 benzaldehyde 
• 78-95-5 chloroacetone 
• 1896-62-4 (E)-benzalacetone 
• 917-54-4 methyllithium 
• 119163-37-0 ((2S,3R)-3-Phenyl-oxiranyl)-pyrrolidin-1-yl-methanone 
• 598-31-2 1-bromoacetone 
• 96650-00-9 trans-N,N-diethyl-3-phenyl-2,3-epoxypropionamide 
• 19202-21-2 1-trans-cinnamoylpyrrolidine 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 53309-95-8 (+/-)-2-amino-4-phenylbut-3-ene 
• 19190-80-8 methyl 3-Phenylglycidate 
• 16812-43-4 bis(trimethylstannyl)methane 
• 937-53-1 (Z)-4-phenylbut-3-en-2-one 
• 536-74-3 phenylacetylene 

Downstream Products

• 98204-74-1 2-(Hydroxy-phenyl-methyl)-1-methyl-cyclopropanol 
• 5381-93-1 1-hydroxy-1-phenyl-3-butanone 
• 146388-50-3 (3S,4R)-3,4-epoxy-4-phenylbutan-2-one 
• 146388-52-5 (2S,3R,4R)-(+)-3,4-epoxy-4-phenyl-2-butanol 
• 146388-51-4 (2S,3S,4S)-(-)-3,4-epoxy-4-phenyl-2-butanol 
• 65-85-0 benzoic acid 
• 93-91-4 1-phenylbutan-1,3-dione 
• 5355-63-5 3-hydroxy-4-phenyl-2-butanone 
• 5381-89-5 1-phenylbutane-2,3-diol 
• 68655-09-4 (Z)-1-hydroxymethylene-1-phenylacetone 

Relevant academic research and scientific papers

A highly enantioselective synthesis of the odorant, 3-hydroxy-4- phenylbutan-2-one

An efficient and highly enantioselective synthesis of 3-hydroxy-4- phenylbutan-2-one was developed involving the asymmetric epoxidation of an enone and hydrogenolysis of an α,β-epoxyketone. 1-Phenyl-3-buten-2-one was epoxidised with t-butyl hydroperoxide using a chiral La-BINOL-Ph3P=O complex as the catalyst to give (3S,4R)- or (3R,4S)- 3,4-epoxy-4-phenylbutan-2- one in ～90% yield and 97% ee. The resultant optically active epoxyketone was reduced in the presence of Pd/C (5 mol%) and H2 (3 bar) in THF at room temperature to produce (S)- or (R)-3-hydroxy-4-phenylbutan- 2-one in ～80% yield with more than 90% enantiomeric excess.

Synthesis of fluorinated materials catalyzed by proline or antibody 38C2 in ionic liquid

The utility of reusable ionic liquid-proline (or aldolase antibody 38C2) reaction system,proceeding the aldol reactions, is described. Further, obtained α-chloro-β-hydroxy compounds were transformed to the optically active α,β-epoxy carbonyl compounds. Th

Water vs. desiccant. Improvement of Yb-BINOL complex catalyzed enantioselective epoxidation of enones

The Yb-BINOL-complex-catalyzed enantioselective epoxidation of α,β- unsaturated ketones (enones) was greatly improved by addition of a small amount of water (ca. 5 equiv to Yb). Optimized conditions and a plausible mechanism of the role of water and molec

Asymmetric epoxidation of chalcone catalyzed by reusable poly-l-leucine immobilized on hydrotalcite

Nanohybrid materials based on polyamino acids immobilized onto inorganic materials are of interest for their potential applications in protein engineering, biomedicine and catalysis. We developed an efficient and eco-friendly new protocol for the immobilization of synthesized poly-l-leucine (PLL) onto rehydrated hydrotalcite (HTr). To do this, we synthesized different PLLs containing both C-terminal and N-terminal groups and compared them with a commercial PLLc. These synthetic polypeptides were immobilized onto HTr in water as the liquid medium with less than 30 min of ultrasound treatment. The obtained PLLs/HTr synzyme showed excellent activity and enantioselectivity when used as a catalyst in the asymmetric Juli-Colonna epoxidation reaction of chalcone. Moreover, these nanohybrid materials based on PLLS did not require any pre-activation time, which were easily separated from the reaction media and, unlike the commercial PLLc-supported catalyst, were reusable, exhibiting high stability after five consecutive runs without any apparent deactivation.

Scoping the triphasic/PTC conditions for the Juliá-Colonna epoxidation reaction

A new, highly efficient procedure for the Juliá-Colonna epoxidation is reported. Based on the original triphasic protocol it is shown that the co-catalysis of the reaction with phase transfer catalysts results in a dramatic increase of reactivity and some

Enantioselective epoxidation of α,β-unsaturated ketones using polymer-supported lanthanoid-BINOL complexes

The immobilization of chiral lanthanum and/or ytterbium complexes using polymer-support is described. The heterogeneous catalysts obtained promote the enantioselective epoxidation of α,β-unsaturated ketones affording the products in good yields with high enantiomeric excess. The catalysts were easily separated from the products by washing with ether and the recovered catalysts promote the enantioselective epoxidation reaction effectively maintaining the high level of enantioselectivity obtained during the first run.

Asymmetric epoxidation of enones employing polymeric α-amino acids in non-aqueous media

Urea-hydrogen peroxide complex in an organic solvent and in the presence of DBU and poly-(L)leucine causes rapid asymmetric epoxidation of the enones 1a, b and d.

Remarkable ligand effect on the enantioselectivity of the chiral lanthanum complex-catalyzed asymmetric epoxidation of enones

The addition of triphenylphosphine oxide significantly enhanced the degree of asymmetric induction (up to 96% ee) in the chiral La-binol- complex-catalyzed epoxidation of enones using tert-butyl hydroperoxide as the oxidant. The new protocol is highly general and practical.

Stereodivergent Access to Enantioenriched Epoxy Alcohols with Three Stereogenic Centers via Ruthenium-Catalyzed Transfer Hydrogenation

The resolution technique of stereodivergent reaction on racemic mixtures (stereodivergent RRM) was employed for the first time in ruthenium complex catalyzed transfer hydrogenation of racemic epoxy ketones, providing a new and very simple method that allows access to enantioenriched epoxy alcohols with three stereogenic centers in a one-step fashion. The protocol features simple reaction conditions, practical operation, ability to scale up, and broad group tolerance.

An efficient Darzens reaction promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)

An efficient DBU promoted Darzens reaction utilising α-haloketones containing an enolizable α′-hydrogen is reported. This method diastereoselectively afforded the corresponding α,β-epoxy ketones good to excellent yields in an one-pot reaction without using any transition metals or additives. Furthermore, haloketones without an α′-hydrogen are also applicable in this reaction.