Cinchona alkaloid-catalyzed asymmetric mannich reactions
US8097750B2 · kind B2 · utility
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Key dates
| Filing date | Dec 12, 2007 |
| Grant date | Jan 17, 2012 |
| Priority date | — |
| Expiry date | Dec 12, 2027 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D333/20
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The instability of carbamate-protected alkyl imines has greatly hampered the development of catalytic asymmetric Mannich reactions suitable for the synthesis of optically active carbamate-protected chiral alkyl amines. A highly enantioselective Mannich reaction with in situ generation of carbamate-protected imines from stable α-amido sulfones catalyzed by an organic catalyst has been developed. This reaction provides a concise and highly enantioselective route converting aromatic and aliphatic aldehydes into optically active aryl and alkyl β-amino acids.
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