Asymmetric carbon-carbon-bond-forming reactions catalyzed by bifunctional cinchona alkaloids
US7582764B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | May 26, 2006 |
| Grant date | Sep 1, 2009 |
| Priority date | — |
| Expiry date | Oct 9, 2026 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C2602/12
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
One aspect of the present invention relates to quinine-based and quinidine-based catalysts. In certain embodiments, the quinine-based and quinidine-based catalysts contain a hydroxy group at the 6′ position. In certain embodiments, the quinine-based and quinidine-based catalysts contain an O-aryl group or an O-aroyl group at the C9 position. In certain embodiments, the quinine-based and quinidine-based catalysts contain an optionally substituted O-diazene group or an optionally substituted O-benzoyl group at the C9 position. In certain embodiments, the quinine-based and quinidine-based catalysts contain a thiourea at the C9 position. In certain embodiments, the quinine-based and quinidine-based catalysts contain an NH(═S)NH-aryl group at the C9 position. Another aspect of the present invention relates to a method of preparing a chiral, non-racemic compound from a prochiral electron-deficient alkene or prochiral imine, comprising the step of: reacting a prochiral alkene or imine 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. In certain embodiments, the nucleophile is a m…
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