253350-07-1

Upstream product

• 24393-56-4 ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 24393-56-4 ethyl p-methoxycinnamate 
• 757227-80-8 3-chloro-3-(4-methoxy-phenyl)-2-oxo-propionic acid ethyl ester 
• 123-11-5 4-methoxy-benzaldehyde 
• 811467-26-2 3-hydroxy-3-(4-methoxy-phenyl)-2-oxo-propionic acid ethyl ester 

Downstream Products

• 757227-88-6 5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester 
• 780795-84-8 ethyl 3-azido-2-hydroxy-3-(4-methoxyphenyl)propanoate 

Relevant academic research and scientific papers

Osmium tetroxide in poly(ethylene glycol) (PEG): A recyclable reaction medium for rapid asymmetric dihydroxylation under Sharpless conditions

PEG (400) has been used as a recyclable and rapid reaction medium for the asymmetric dihydroxylation of olefins; Sharpless ligand is efficiently recovered and recycled with good enantioselectivity.

Manganese catalyzed cis-dihydroxylation of electron deficient alkenes with H2O2

A practical method for the multigram scale selective cis-dihydroxylation of electron deficient alkenes such as diethyl fumarate and N-alkyl and N-aryl-maleimides using H2O2 is described. High turnovers (>1000) can be achieved with this efficient manganese based catalyst system, prepared in situ from a manganese salt, pyridine-2-carboxylic acid, a ketone and a base, under ambient conditions. Under optimized conditions, for diethyl fumarate at least 1000 turnovers could be achieved with only 1.5 equiv. of H2O2 with d/l-diethyl tartrate (cis-diol product) as the sole product. For electron rich alkenes, such as cis-cyclooctene, this catalyst provides for efficient epoxidation.

A recyclable dendritic osmium catalyst for homogeneous dihydroxylation of olefins

A series of osmate (OsO42-) core dendrimers was prepared by an ion-exchange technique through the mixing of K 2OsO4 and a bis(quaternary ammonium bromide) core dendrimer, which consisted of poly(benzyl ether) dendron. By employing an osmate core dendrimer as a homogeneous catalyst, dihydroxylation reactions of olefins proceeded rapidly, and the dendritic osmium catalyst was recovered by reprecipitation and then reused. Furthermore, a dendritic effect on the recyclability of a catalyst was observed. In the case of asymmetric dihydroxylation reactions, the corresponding diol was obtained in a high chemical yield with a fair enantiomeric excess (ee). In this case, not only the dendritic osmium catalyst but also the chiral ligand could be recovered by reprecipitation and reused efficiently up to five times.

Novel synthesis of 4-chloro-3-hydroxy-2-pyrone by the reaction of acetonide protected 4,5-dihydroxy-2-chloroglycidic ester with magnesium chloride

Treatment of acetonide protected 4,5-dihydroxy-2-chloroglycidic ester with magnesium chloride gave 4-chloro-3-hydroxy-2-pyrone in excellent to good yields. Treatment of acetonide protected 4,5-dihydroxy-2-chloroglycidic ester with magnesium chloride gave 4-chloro-3-hydroxy-2-pyrone in excellent to good yields.

Catalytic asymmetric dihydroxylation of alkenes using silica gel supported cinchona alkaloid

Immobilization of 3,6-bis(9-O-dihydroquinyl)pyridazine and 3,6-bis(9-O-dihydroquinidyl) pyridazine on silica gel support has been reported. The use of immobilized auxiliary has lead to comparable rate with that of the homogeneous catalytic AD of alkenes, however with lower ee.