Cinchona-alkaloid-based catalysts, and asymmetric alcoholysis of cyclic anhydrides using them
US7531662B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Jun 10, 2004 |
| Grant date | May 12, 2009 |
| Priority date | — |
| Expiry date | Jul 19, 2025 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D453/04
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
One aspect of the present invention relates to cinchona-alkaloid-based catalysts. A second aspect of the invention relates to a method of preparing a derivatized cinchona alkaloid catalyst by reacting a cinchona-alkaloid with base and a compound that has a suitable leaving group. Another aspect of the present invention relates to a method of preparing a chiral, non-racemic compound from a prochiral cyclic anhydride or a meso cyclic anhydride, comprising the step of: reacting a prochiral cyclic anhydride or a meso cyclic anhydride with a nucleophile in the presence of a catalyst; wherein said prochiral cyclic anhydride or meso cyclic anhydride comprises an internal plane of symmetry or point of symmetry or both; thereby producing a chiral, non-racemic compound; wherein said catalyst is a derivatized cinchona-alkaloid. Yet another aspect of the present invention relates to a method of kinetic resolution, comprising the step of: reacting a racemic cyclic anhydride with an alcohol in the presence of a derivatized cinchona-alkaloid catalyst.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.