Title:
MANUFACTURE OF OPTICAL ARYLPROPIONIC ACID ESTER
Document Type and Number:
Japanese Patent JPS5826841
Kind Code:
A
Abstract:
There is described a process for the preparation of methyl esters of arylpropionic acids, through carbonylation of the corresponding vinylaromatic compound of formula (I):
R - CH = CH2 (I)
wherein R stands for an aryl group, preferably a phenyl group, a diphenyl, a naphthyl group, also substituted with inert groups, which is made to react with carbon monoxide and methyl alcohol in the presence of a palladium catalyst chosen from amongst complexes of formula (II):
PdLnL min m (II)
wherein L stands for the optically active diphenylneomenthylphosphine; L min represents a conjugated olefinic ligand containing electron-attracting groups, n is an integer chosen between 1 and 3, m is an integer chosen from between 0 and 2, such that n+m=3, associated with the trifluoro acetic acid; and a palladium salt chosen from amongst the carboxylic acids and/or acetylacetonate associated with the optically active diphenyl-neomenthylphosphine and with trifluoroacetic acid, at substantially atmospheric pressure and at a temperature comprised between 20 DEG and 80 DEG C. The reaction medium consists of the methyl alcohol in excess associated or not with alcoholic solvents (butanol) or ethers (anisol). There is dealt with particular regioselective and enantioselective catalysis conditions.
The products thereby obtained consist of esters of arylpropionic acids which, whether as such or in the form of the corresponding acids obtainable from them, find their use as intermediates in the synthesis of organical compounds, in general, with particular purpose for pharmaceutical products thanks to the high regioselectivity associated with a considerable enantioselectivity, and for which the aspect of the optical selectivity is of the highest therapeutical and economical interest.
Inventors:
JIYUZETSUPE KOMETSUTEI
JIYAN PAORO KIUSORI
JIYAN PAORO KIUSORI
Application Number:
JP13481482A
Publication Date:
February 17, 1983
Filing Date:
August 03, 1982
Export Citation:
Assignee:
MONTEDISON SPA
International Classes:
B01J31/00; C07C59/64; C07C67/38; C07C69/003; C07C69/612; C07C; (IPC1-7): B01J31/22; C07C67/38; C07C69/003
Attorney, Agent or Firm:
Motohiro Kurauchi