Asymmetric Michael and Aldol additions using bifunctional cinchona-alkaloid-based catalysts
US7312335B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | May 27, 2005 |
| Grant date | Dec 25, 2007 |
| Priority date | — |
| Expiry date | Jul 17, 2025 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C2602/08
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
One aspect of the present invention relates to quinine-based and quinidine-based catalysts. Another aspect of the invention relates to a method of preparing a derivatized quinine-based or quinidine-based catalyst comprising 1) reacting quinine or quinidine with base and a compound that has a suitable leaving group, and 2) converting the ring methoxy group to a hydroxy group. Another aspect of the present invention relates to a method of preparing a chiral, non-racemic compound from a prochiral electron-deficient alkene or azo compound or prochiral aldehyde or prochiral ketone, comprising the step of: reacting a prochiral electron-deficient alkene or azo compound or prochiral aldehyde or prochiral ketone with a nucleophile in the presence of a catalyst; thereby producing a chiral, non-racemic compound; wherein said catalyst is a derivatized quinine or quinidine. Another aspect of the present invention relates to a method of kinetic resolution, comprising the step of: reacting racemic chiral alkene with a nucleophile in the presence of a derivatized quinine or quinidine.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.