Rhodia Chirex, Inc.

Rhodia Pharma Solutions Inc.

Serge Jasmin

Yi Liu

Eric N Jacobsen

Jay Larrow

Salvatore Anthony Marchese

Marcello Di Mare

Marcello DiMare

The present invention provides a process for the preparation of an enantiomerically enriched non-racemic chiral diol and an enantiomerically enriched non-racemic chiral epoxy compound by a hydrolytic kinetic resolution reaction. The process includes the step of contacting oxygen and mixture including a racemic chiral epoxy compound, a non-racemic Co(II) complex catalyst, an aromatic carboxylic acid and water, at a temperature and length of time sufficient to produce a mixture of said non-racemic chiral diol and said non-racemic chiral epoxy compound. The present invention also provides a process for the preparation of an enantiomerically enriched non-racemic chiral diol and an enantiomerically enriched non-racemic chiral epoxy compound by a hydrolytic kinetic resolution reaction. This process includes the step of: contacting a racemic chiral epoxy compound and water in the presence of a non-racemic complex of Co(III) having an aryl carboxylate counter-anion, at a temperature and length of time sufficient to produce a mixture of said non-racemic chiral diol and said non-racemic chiral epoxy compound.

Hydrolytic kinetic resolution of epoxides

A method for stereoselective chemical synthesis, includes the steps of: (A) reacting a nucleophile and chiral or prochiral cyclic subtrate, said substrate comprising a carbocycle or a heterocycle having a reactive center susceptible to nucleophilic attack by the nucleophile, in the presence of a chiral non-racemic catalyst to produce a product mixture comprising a stereomerically enriched product wherein the product mixture further comprises a catalyst residue, at least a portion of the catalyst residue is in a first oxidation state, and the catalyst residue in the first oxidation state is active in catalyzing degradation of the stereoisomerically enriched product, and (B) chemically or electochemically changing the oxidation state of the catalyst residue from the first oxidation state to a second oxidation state, wherein catalyst residue in the second oxidation state is less active in catalyzing degradation of the stereoisomerically enriched product than is catalyst residue in the first oxidation state. The method reduces erosion of the chiral purity of the stereoisomerically enriched product and reduces the chemical transformation to side products of the stereoisomerically enriched product and co-product(s). The deactivated catalyst is recoverable and recyclable.

Kinetic resolution method

Growing community of inventors

Watertown, MA, United States of America

Serge Jasmin