Abstract
A systematic study of the effect of substitution within the beta-amino acid framework indicates that both beta(2)- and beta(3)-amino acids catalyse the Hajos-Parrish-Eder-Sauer-Wiechert reaction with poor to reasonable levels of enantioselectivity. These results led to the evaluation of the conformationally constrained beta-amino acid (1R,2S)-cispentacin, which catalyses the Hajos-Parrish-Eder-Sauer-Wiechert reaction with comparable or higher levels of enantioselectivity to L-proline.
| Original language | English |
|---|---|
| Pages (from-to) | 3190-3200 |
| Number of pages | 11 |
| Journal | Organic & Biomolecular Chemistry |
| Volume | 5 |
| Issue number | 19 |
| DOIs | |
| Publication status | Published - 2007 |
Keywords
- INTERMOLECULAR ALDOL REACTIONS
- MICHAEL ADDITION-REACTIONS
- ASYMMETRIC-SYNTHESIS
- ALPHA,BETA-UNSATURATED ALDEHYDES
- NUCLEOPHILIC CARBENES
- GAMMA-BUTYROLACTONES
- PROLINE DERIVATIVES
- KINETIC RESOLUTION
- LITHIUM AMIDES
- NITRO-OLEFINS
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