Abstract
The proline-catalyzed addition of various aliphatic aldehydes to sterically hindered 2-aryl-substituted 3H-indol-3-ones affords 2,2-disubstituted 2,3-dihydro-1H-indol-3-one derivatives with excellent enantioselectivities. In addition, the synthesis of a chiral derivative, (S)-2-(2-bromophenyl)-2,3- dihydro-2-(2-hydroxyethyl)-1H-indol-3-one, which can be used as an intermediate for the preparation of the natural product hinckdentine A was accomplished with a high level of enantioselectivity.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 2296-2303 |
| Number of pages | 8 |
| Journal | Helvetica Chimica Acta |
| Volume | 95 |
| Issue number | 11 |
| DOIs | |
| State | Published - Nov 2012 |
| Externally published | Yes |
Keywords
- Catalysis
- Hinckdentine A
- Indol-2-acetaldehyde
- Mannich reaction
- Proline
ASJC Scopus subject areas
- Catalysis
- Biochemistry
- Drug Discovery
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry