C - Chemistry – Metallurgy – 12 – P
Patent
C - Chemistry, Metallurgy
12
P
C12P 41/00 (2006.01)
Patent
CA 2316294
A process for resolving racemic diesters of (R,S)(~)-5-hydroxy-3-(4'- hydroxyphenyl)-1,1,3-trimethylindane is disclosed. The process utilizes a microbial enzyme derived from Chromobacterium viscosum to catalyze the enantioselective and regioselective hydrolysis of the (S)(-)-enantiomer of the racemic mixture to its corresponding monoester at a faster rate than the (R)(+)-enantiomer. A substantially pure (S)(-)-indane monoester is thereby formed, while the (R)(+)-indane diester remains unreacted. The (S)(+)-monoester and the (R)(+)-diester can then be hydrolyzed using conventional techniques to form optically active (R)(+)- and (S)(-)-5-hydroxy-3-(4'-hydroxyphenyl)- 1,1,3--trimethylindane enantiomers for use as monomers in the synthesis of chiral polymers.
L'invention concerne un procédé de dédoublement de diesters racémiques de (R,S)(+/-)-5-hydroxy-3-(4'-hydroxyphényl)-1,1,3-triméthylindane, dans lequel on utilise une enzyme microbienne dérivée de Chromobacterium viscosum, afin de catalyser l'hydrolyse énantiosélective et régiosélective du (S)(-)-énantiomère du mélange racémique et former le monoester correspondant de celui-ci plus rapidement que le (R)(+)-énantiomère. On forme ainsi un monoester sensiblement pur de (S)(-)-indane, tandis que le diester de (R)(+)-indane ne subit pas de réaction. On peut ensuite hydrolyser le (S)(-)-monoester et le (R)(+)-diester à l'aide de techniques classiques, afin de former des énantiomères de (R)(+)- et (S)(-)-5-hydroxy-3-(4'-hydroxyphényl)-1,1,3-triméthylindane, optiquement actifs, utiles en tant que monomères dans la synthèse de polymères chiraux.
Kazlaukas Romas J.
Zhang Xiaoming
Molecular Optoelectronics Corporation
Ridout & Maybee Llp
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