78626-51-4

Upstream product

• 131469-58-4 methyl 2-benzoyloxirane-2-carboxylate 
• 1239450-42-0 2-benzoylamino-3-methoxy-3-oxo-propanol benzoate 
• 600-22-6 pyruvic acid methyl ester 
• 98-88-4 benzoyl chloride 
• 81077-03-4 methyl benzoyloxy-α-diazopropionate 

Downstream Products

• 58653-96-6 2-benzoyloxy-propionic acid methyl ester 
• 912463-01-5 (Z)-1-(2-(acetoxymethyl)-4-(tert-butoxycarbonylamino)-3-methylphenyl)-3-methoxy-3-oxoprop-1-en-2-yl benzoate 

Relevant academic research and scientific papers

Triphenylphosphine-mediated synthesis of methyl 2-aroyloxypropenoates from 2-aroyl-2-methoxycarbonyloxiranes

A new synthesis of several 2-aroyloxypropenoic acid methyl esters 5 by the reaction of 2-aroyl-2-methoxycarbonyloxiranes 2 with triphenylphosphine in tetrahydrofuran has been described.

Synthesis of new captodative alkenes: Alkyl 2-aroyloxy acrylates - Structure, and reactivity in Diels - Alder cycloadditions

Novel captodative alkenes, namely the methyl and ethyl esters of 2-aroyloxyacrylic acids, 2 and 3, have been prepared. Their reactivity and selectivity have been evaluated in Diels - Alder cycloadditions with unsymmetrical dienes, which generate the corresponding adducts with high regioselectivity. No significant stereoselectivity was observed in the reaction with cyclopentadiene (9), although Lewis acid catalysis improved the exo/endo isomeric ratio. Structural and electron spectroscopic studies of these alkenes are supported by MO calculations. FMO theory accounts for the regioselectivity observed with isoprene (7), and the reactivity seen in Diels - Alder additions correlates with the stabilization of the relevant vacant π· MO in these alkenes, which is mainly due to the electron-withdrawing group.

CATALYZED INSERTION REACTIONS OF SUBSTITUTED Α-DIAZOESTERS. A NEW SYNTHESIS OF CIS-ENOATES

The decomposition of α-diazoesters is notably catalyst-dependent; with rhodium (II) carboxylates a stereoselective insertion reaction leads to the title structures in high yield.