161512-01-2

Upstream product

• 154902-05-3 (S,S,S)-(+)-erythro-trans-1-phenyl-2,3-epoxybutan-1-ol 
• 52755-39-2 (2E)-1-phenylbut-2-en-1-ol 
• 495-41-0 1-phenylbut-2-en-1-one 
• 35660-91-4 (E)-1-phenyl-2-buten-1-one 

Downstream Products

• 34501-28-5 (+/-)-(RS)-((2SR,3SR)-3-methyloxiranyl)-phenylmethanol 

Relevant academic research and scientific papers

Asymmetric epoxidation of α,β-unsaturated ketones with hydrogen peroxide catalyzed by axially chiral guanidine base

The enantioselective epoxidation of α,β-unsaturated ketones with hydrogen peroxide was demonstrated using axially chiral guanidine as a base catalyst. Hydrogen peroxide can be utilized as a cost-effective and atom-efficient oxidant in the present catalyti

On the mechanism of asymmetric epoxidation of enones catalyzed by a,a-l-diarylprolinols: A theoretical insight

The mechanism of the asymmetric epoxidation of enones with tert-butyl hydroperoxide promoted by a,a-l-diarylprolinols has been studied by second order Moller-Plesset perturbation theory (MP2) and density functional theory (DFT) computations. The non-coval

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.

Stabilized α-helix-catalyzed enantioselective epoxidation of α,β-unsaturated ketones

(Equation Presented). Chiral cyclic α-amino acid containing oligopeptide catalyzed highly enantioselective epoxidation of α,β-unsaturated ketones and the α-helical secondary structure of the peptide catalyst were revealed by X-ray crystallographic analysis.

Asymmetric epoxidation of substituted chalcones and chalcone analogues catalyzed by α-d-glucose- and α-d-mannose-based crown ethers

The chiral monoaza-15-crown-5 lariat ethers annellated to methyl-4,6-O-benzylidene-α-d-glucopyranoside-1 or mannopyranoside 2 have been applied as phase-transfer catalysts in the epoxidation of substituted chalcones and chalcone analogues with tert-butylhydroperoxide resulting in significant asymmetric induction. It was found that the position of the substituents in the aromatic ring of the chalcone had an influence both on the chemical yields and enantiomeric excesses. The lowest enantioselectivities (62-83% ee) were found in the case of ortho-substituted model compounds. The highest ee values (ee of 83-97%) were obtained in the case of para-substituted models. From among the chalcone analogues, the maximum ee (90-92%) was detected for the model compound having α-tert-butyl- and β-aryl groups. Using glucose-based crown ether 1, formation of the (-)-enantiomer was preferred, while applying mannose-based 2 as the catalyst, the (+)-enantiomer was in excess.

Asymmetric oxidations of electron-poor alkenes promoted by the β-amino alcohol/TBHP system

The asymmetric oxyfunctionalization of alkenes is a fundamental process in synthetic organic chemistry. In this contribution, we review our findings on the enantioselective organocatalyzed oxidation of electron-poor alkenes. Readily or commercially available β-amino alcohols displayed catalytic activity in the asymmetric epoxidation of α,β-enones and β-peroxidation of nitroalkenes with tert-butyl hydroperoxide (TBHP) as the oxidant. The corresponding epoxides and peroxides were isolated in good to high yield and enantioselectivity. Georg Thieme Verlag Stuttgart.

Bis(3,5-dimethylphenyl)-(S)-pyrrolidin-2-ylmethanol: An improved organocatalyst for the asymmetric epoxidation of α,β-enones

The asymmetric epoxidation of α,β-enones by the readily available bis(3,5-dimethylphenyl)-(S)-pyrrolidin-2-ylmethanol and tert-butyl hydroperoxide (TBHP) is described. Stereoelectronic substitution on the aryl moiety of diaryl-2-pyrrolidinemethanols was f

Enantioselective epoxidation of α,β-enones by electrophilic activation with a BINOL-zinc catalyst

The combination of BINOL and a dialkylzinc reagent R2Zn affords, in situ, a catalyst for homogeneous epoxidation of (E)-α,β-enones to the corresponding trans-epoxy ketones. tert-Butyl hydroperoxide (TBHP) and cumene hydroperoxide (CMHP) are eff

Diaryl-2-pyrrolidinemethanols catalyzed enantioselective epoxidation of α,β-enones: new insight into the effect of structural modification of the catalyst on reaction efficiency

Catalytic enantioselective epoxidation of α,β-unsaturated ketones promoted by diaryl-2-pyrrolidinemethanols and tert-butyl hydroperoxide (TBHP) is described. Investigation on structural modifications of the diaryl-2-pyrrolidinemethanols showed that fine t

Enantioselective epoxidation of α,β-enones promoted by α,α-diphenyl-L-prolinol as bifunctional organocatalyst

(Chemical Equation Presented) An operationally simple and mild protocol for the catalytic enantioselective epoxidation of α,β-unsaturated ketones has been established using commercially available α,α- diphenyl-L-prolinol as bifunctional organocatalyst and tert-butyl hydroperoxide (TBHP) as oxidant. The epoxides have been obtained in good yields and with up to 80% ee.