190961-74-1

Upstream product

• 852609-74-6 3-chloro-4-hydroxy-4-phenylbutan-2-one 
• 917-54-4 methyllithium 
• 681121-99-3 (2R,3S)-3-Phenyl-oxirane-2-carboxylic acid diphenylamide 
• 100-52-7 benzaldehyde 
• 78-95-5 chloroacetone 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 67-64-1 acetone 
• 17488-65-2 4-phenylbut-3-en-2-ol 
• 246236-69-1 (E)-1-((2R,5R)-2,5-Dimethyl-pyrrolidin-1-yl)-3-phenyl-propenone 
• 102-92-1 Cinnamoyl chloride 
• 1896-62-4 (E)-benzalacetone 
• 246236-71-5 ((2R,5R)-2,5-Dimethyl-pyrrolidin-1-yl)-((2R,3S)-3-phenyl-oxiranyl)-methanone 

Downstream Products

• 190912-78-8 (-)-(1S,2R,3S)-1,3-Diphenyl-1,2-epoxybutan-3-ol 

Relevant academic research and scientific papers

Asymmetric Cascade Catalysis with Chiral Polyoxometalate-Based Frameworks: Sequential Direct Aldol and Epoxidation Reactions

Catalytic asymmetric cascade reactions in which the substrates are transferred through well-choreographed consecutive independent steps by a single catalyst have received increasing interest. By incorporating a chiral organocatalyst pyrrolidine, an oxidat

Enzymatic cascades for the stereo-complementary epimerisation of in situ generated epoxy alcohols

The synthesis of optically pure secondary epoxy alcohols from racemic allylic alcohols using a single whole-cell biocatalyst of recombinant Escherichia coli coexpressing three oxidoreductases is described. The cascade involves the concurrent action of a styrene monooxygenase that catalyzes the formation of the chiral epoxy group, and two alcohol dehydrogenases that fulfil the epimerisation of the hydroxy group. Two sets of alcohol dehydrogenases were each applied to couple with styrene monooxygenase in order to realize the epimerisation in a stereo-complementary manner. Excellent enantio- and diastereo-selectivities were achieved for most of the 12 substrates.

Switchable asymmetric bio-epoxidation of α,β-unsaturated ketones

Efficient asymmetric bio-epoxidation of electron-deficient α,β-unsaturated ketones was realized via a tandem reduction-epoxidation-dehydrogenation cascade, which proceeds in a switchable manner to afford either chiral epoxy ketones or allylic epoxy alcoho

A new class of bifunctional chiral phase transfer catalysts for highly enantioselective asymmetric epoxidation of α,β-unsaturated ketones at ambient temperature

A new type of bis-quaternary ammonium bromide as chiral multifunctional phase transfer catalysts derived from readily available inexpensive cinchona alkaloids has been developed and evaluated for the enantioselective asymmetric epoxidation of various chalcones in the presence of lower concentrations of various oxidants, bases, solvents and ambient temperature conditions. Under optimized reaction conditions, highest chemical yields of up to 98% along with the excellent enantioselectivities of about 99% were obtained by using the cinchona based chiral multifunctional phase transfer catalysts.

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.

Functionalization of BINOL and application in the homo- and heterogeneous enantioselective epoxidation of α,β-unsaturated ketones

The selective functionalization of BINOL derivatives with 3-(dimethylamino)prop-1-yn-1-yl is described. The corresponding La and Yb complexes were evaluated toward the epoxidation of α,β-unsaturated ketones. The Yb-complexes display the highest catalytic

Functionalization of BINOL and application in the homo- and heterogeneous enantioselective epoxidation of α,β-unsaturated ketones

The selective functionalization of BINOL derivatives with 3-(dimethylamino)prop-1-yn-1-yl is described. The corresponding La and Yb complexes were evaluated toward the epoxidation of α,β-unsaturated ketones. The Yb-complexes display the highest catalytic activity and selectivity, affording the expected chiral epoxides in quantitative yields and up to 90% ee in homogeneous conditions, and 93% ee when supported on silica gel.

Highly enantioselective proline-catalysed direct aldol reaction of chloroacetone and aromatic aldehydes

Ready salted proline: The combination of proline and an achiral triazabicyclodecene-derived guanidinium salt permits, for the first time, the direct aldol reaction of chloroacetone and aromatic aldehydes (see scheme). The resulting chlorohydrins are formed with high regio-, diastereo- and enantioselectivity. This procedure is experimentally simple and green, working without solvent, in test tubes placed inside a standard laboratory fridge without agitation or mechanical stirring.

Enantioselective epoxidation of α,β-unsaturated ketones catalyzed by stapled helical l-Leu-based peptides

Stapled helical l-leucine-based heptapeptides were synthesized and used as catalysts for the enantioselective epoxidation of α,β-unsaturated ketones. All N-terminal free stapled peptides were successfully used as chiral catalysts. Among them, the use of H-hS3,7hS-10 gave epoxide products with high enantioselectivities of up to 99% ee. Furthermore, the dominant conformations of the N-terminal protected stapled peptides R 3,7R-10 and hS3,7hS-10 were investigated by 1H NMR, IR, CD spectra, and X-ray crystallographic analysis. The peptide R3,7R-10 formed a right-handed (P) α-helix in solution and in the crystalline state, while hS 3,7hS-10 formed a right-handed (P) 310-helix in solution.

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.