84034-01-5

Upstream product

• 36597-08-7 (E)-4-methyl-1-phenyl-2-penten-1-one 
• 78-84-2 isobutyraldehyde 
• 70-11-1 α-bromoacetophenone 
• 98-86-2 acetophenone 
• 532-27-4 1-chloroacetophenone 
• 7316-69-0 1-phenyl-4-methyl-2-penten-1-one 

Downstream Products

• 7316-69-0 1-phenyl-4-methyl-2-penten-1-one 
• 115827-02-6 3-hydroxy-4-methyl-1-phenylpentan-1-one 
• 13988-65-3 4-methyl-1-phenyl-pentane-1,3-dione 

Relevant academic research and scientific papers

Asymmetric Epoxidation of Enones Promoted by Dinuclear Magnesium Catalyst

Asymmetric synthesis with cheaper and non-toxic alkaline earth metal catalysts is becoming an important and sustainable alternative to conventional catalytic methodologies mostly relying on precious metals. In spite of some sustainable methods for enantioselective epoxidation of enones, the development of a well-defined and efficient catalyst based on magnesium complexes for these reactions is still a challenging task. In this perspective, we present the application of chiral dinuclear magnesium complexes for asymmetric epoxidation of a broad range of electron-deficient enones. We demonstrate that the in situ generated magnesium-ProPhenol complex affords enantioenriched oxiranes in high yields and with excellent enantioselectivities (up to 99% ee). Our extensive study verifies the literature data in this area and provides a step forward to better understand the factors controlling the oxygenation process. Elaborated catalyst offers mild reaction conditions and a truly wide substrate scope. (Figure presented.).

Quest for Efficient Catalysts based on Zinc tert-Butyl Peroxides for Asymmetric Epoxidation of Enones: C2- vs C1-Symmetric Auxiliaries

Zinc tert-butyl peroxide-based catalysts for the asymmetric epoxidation of enones using tert-butyl hydroperoxide as an oxidant have been developed. A comparative study of chiral monoanioninc N,N′-bidentate ligands, C2-symmetric bisoxazolinates and C1-symmetric enaminooxazolinates, revealed excellent performance of C1-symmetric auxiliary ligands on catalytic asymmetric epoxidation of enones (up to 96% yield, 91% ee).

Darzens reaction rate enhancement using aqueous media leading to a high level of kinetically controlled diastereoselective synthesis of steroidal epoxyketones

Darzens reactions between halocarbonyls and aldehydes have been carried out in water in the presence of a Li+-containing base, a phase-transfer catalyst, and granular polytetrafluoroethylene under mechanical stirring. Reactions using both aromatic and aliphatic aldehydes produced epoxides stereoselectively in good to excellent yields. This is the first time that aliphatic aldehydes with α-H have been used in aqueous Darzens reactions. The Darzens reactions were much faster in water than in organic solvents. This aqueous rate enhancement occurred for Darzens reactions between enantiopure steroidal haloketones and aldehydes, yielding enantiopure spiroepoxides with a high level of kinetically controlled diastereoselectivity. Chromatography was avoided in the purifications of the steroidal spiroepoxides. This is an example of preparing enantiopure epoxyketones via aqueous Darzens reaction using chiral α-haloketone substrates.

Michael-type addition of hydroxide to alkynylselenonium salt: Practical use as a ketoselenonium ylide precursor

A novel synthetic method of ketodiphenylselenonium ylide from alkynylselenonium salt is described. A reaction of alkynylselenonium salt, hydroxide ion, and aldehyde in the presence of silver triflate and triethylamine gave oxiranylketones just as a trans-

Triphase catalysis in epoxidation of α,β-enones with polymer bound quaternary ammonium salt

A polymer bound quaternary ammonium salt, prepared from DABCO and Merrifield resin, catalyzed an epoxidation of a variety of α,β-enones with aqueous H2O2.

Exploratory Study on Photoinduced Single Electron Transfer Reactions of α,β-Epoxy Ketones with Amines

Photoinduced single electron transfer (SET) reactions of α,β-epoxy ketones have been studied using alkylamine electron donors.Irradiation of chalcone epoxide 1 with triethylamine (TEA) afforded β-diketone 2 and β-hydroxy ketne 3.Photoreaction of 1 with TEA in MeOH resulted in a slightly increased product ratio (3/2) compared with that in MeCN.When 1,4-diazabicyclooctane (DABCO) was used instead of TEA, a decrease in the yield of 3 was observed.Only 2 was obtained on irradiation of a solution of 1 in TEA and MeCN containing LiClO4.Studies of photoreactions of dypnone epoxide 9, benzoylisopropylethylene epoxide 12, and acrylophenone epoxide 15 indicate that the nature of β-substituent also influences the product distribution.It was also found that 1,6-bis(dimethylamino)pyrene (BDMAP) sensitizes the photoreaction of 1 in the presence of TEA to produce 2.Based on the results obtained, a reaction mechanism involving selective Cα-O bond cleavage of intermediate α,β-epoxy ketone anion radicals is proposed.

SYNTHETIC CONTROL LEADING TO CHIRAL COMPOUNDS

A highly diastereoselective cross aldol reaction is developed using divalent tin enolates formed from stannous trifluoromethanesulfonate and carbonyl compounds.The reaction is extended to a highly enantioselective cross aldol reaction employing chiral dia

STEREOSELECTIVE SYNTHESIS OF CIS-α,β-EPOXYKETONES VIA DIVALENT TIN ENOLATE

A convenient method for the stereoselective synthesis of cis-β-substituted-α,β-epoxyketone is established employing Sn(OTf)2 mediated cross aldol reaction between α-bromoketone and aldehyde followed by successive treatment of the adduct with KF-dicyclohex