132633-82-0

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 96-34-4 methyl chloroacetate 
• 20754-20-5 3-p-tolyl-acrylic acid methyl ester 
• 67-56-1 methanol 
• 1504-75-2 3-(4-methylphenyl)acrylaldehyde 
• 33984-93-9 3-(4-methylphenyl)-2-cyanooxirane 

Downstream Products

• 195616-15-0 (2S,3R)-3-(4-methylphenyl)-2,3-epoxypropionamide 

Relevant academic research and scientific papers

Regioselective syntheses of 3-hydroxy-4-aryl-3,4,5-trihydro-2H-benzo[b][1,4]diazepin-2(1H)-ones and 3-benzylquinoxalin-2(1H)-ones from arylglycidates when exposed to 1,2-diaminobenzenes

Representatives of two pharmacologically significant classes of compounds – 3-hydroxy-4-aryl-3,4,5-trihydro-2H-benzo[b][1,4]diazepin-2(1H)-ones and 3-benzylquinoxalin-2(1H)-ones – obtained in reactions of 1,2-diaminobenzenes with methyl 3-arylglycidates in boiling acetic acid. Substituents in arylglycidates determine the direction of processes. Electron withdrawing substituents (NO2), halogen atoms (Cl, Br, F), as well as the absence of substituents, provide the formation of benzo[b][1,4]diazepin-2(1H)-one derivatives, and electron donating groups (OMe, Me) contribute to the formation of 3-benzylquinoxalin-2(1H)-ones. As a result, a new rare representatives of 3-hydroxy-4-aryl-3,4,5-trihydro-2H-benzo[b][1,4]diazepin-2(1H)-ones were obtained and a new method for producing 3-benzylquinoxalin-2(1H)-ones has been proposed.

Highly efficient asymmetric synthesis of α,β-epoxy esters via one-pot organocatalytic epoxidation and oxidative esterification

Highly enantioselective synthesis of α,β-epoxy esters was achieved via one-pot organocatalytic epoxidation and consequent oxidative esterification. Excellent enantioselectivities (up to 99% ee) and good yields were obtained for a variety of α,β-epoxy esters. The method was readily scaled. Furthermore the product was applied towards the synthesis of (-)-clausenamide with excellent enantioselectivities (>99% ee).

A catalytic asymmetric synthesis of chiral glycidic acid derivatives through chiral dioxirane-mediated catalytic asymmetric epoxidation of cinnamic acid derivatives

A novel and practical asymmetric synthesis of chiral glycidic acid derivatives involving methyl (2R,3S)-3-(4-methoxyphenyl)glycidate ((2R,3S)-2a), a key intermediate for diltiazem hydrochloride (1), was developed. Treatment of methyl (E)-4-methoxycinnamate ((E)-3a) with chiral dioxirane, generated in situ from a catalytic amount (5 mol %) of an 11-membered C2-symmetric binaphthyl ketone (R)-7a, provided (2R,3S)-2a in 92% yield and 80% ee. Other cinnamic acid esters and amides were epoxidized by the use of the same procedure to give the corresponding chiral glycidic acid derivatives with up to 95% yield and 92% ee. Higher enantioselectivities in the asymmetric epoxidation of (E)-cinnamates than that of (E)-stilbene derivatives were observed and were proposed to be attributed to a dipole-dipole repulsion between oxygen atoms of an ester group in the cinnamates and those of the lactone moieties in the binaphthyl dioxirane.

A novel synthesis of a key intermediate for diltiazem

A practical synthesis of methyl (2R,3S)-3-(4-methoxyphenyl)glycidate (-)-2a, a key intermediate for diltiazem (3), was described. Treatment of methyl (E)-4-methoxycinnamate (E)-1a with chiral dioxirane, generated in situ from a catalytic amount of an 11-membered C2-symmetric binaphthyl ketone 7a, provided (-)-2a in 78% ee and 89% yield. The crude mixture of (-)-2a and 7a was efficiently separated by the use of novel equipment performing continuous dissolution and crystallization to furnish the optically pure (-)-2a (>99% ee) and recovery of 7a in 64 and 88% yields, respectively.

Process for preparing optically active 3-phenylglycidic acid esters

A process for preparing optically active 3-phenylglycidic acid esters comprising reacting a racemic trans-3-phenylglycidic acid with an alkanol in the presence of a hydrolase to esterify preferentially either (2S, 3R) isomer or (2R, 3S) isomer of said rac

Process for preparing optically active 3-phenylglycidic acid esters

There is disclosed a process for preparing optically active 3-phenylglycidic acid ester compound, which comprises permitting a culture broth, cells or treated cells of a microorganism having an ability of stereoselectively hydrolyzing a (2R, 3S)-3-phenylglycidic acid ester compound to act on a racemic 3-phenylglycidic acid ester compound which may also have a substituent on the phenyl group, thereby hydrolyzing the (2R, 3S) optically active isomer and separating and collecting the (2S, 3R) antipode from the reaction mixture.

REACTION OF 4-SUBSTITUTED BENZALDEHYDES AND ACETOPHENONES WITH CHLOROACETONITRILE

Under conditions of phase-transfer catalysis or in homogeneous solution of potassium tert-butoxide the title compounds give stereoisomeric mixtures of substituted 2,3-epoxy nitriles III and IV.Alkaline hydrolysis of epoxy nitriles IV afforded the corresponding 2-arylpropanals in low yields.On treatment with methanol and potassium carbonate, epoxy nitriles III and IV were converted into epoxy esters in good yields.