Abstract
New enantiomerically pure 3-naphthylaminomethylpyrrolidines (8), (9), (14) and (15) were obtained through simple steps starting from chiral 4- ethenylpyrrolidin-2-ones (2) and (3). On the other hand, starting from pyrrolidine (16), an epimerisation reaction occurred, which was explained through formation of the bicyclic ammonium salt (18). Nucleophilic addition of Et2Zn to benzaldehyde, carried out in the presence of 8, gave (S)-1- phenyl-1-propanol in 28% e.e.
| Original language | English |
|---|---|
| Pages (from-to) | 2463-2470 |
| Number of pages | 8 |
| Journal | Heterocycles |
| Volume | 51 |
| Issue number | 10 |
| Publication status | Published - Oct 1 1999 |
ASJC Scopus subject areas
- Organic Chemistry
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Fava, C., Galeazzi, R., Mobbili, G., & Orena, M. (1999). New chiral 3-naphthylaminomethylpyrrolidines: An unexpected epimerisation reaction. Heterocycles, 51(10), 2463-2470.