Abstract
Intramolecular conjugate addition of γ-substituted (E)- α,β-unsaturated ketones with a Lewis acid (BF3· OEt2) selectively afforded trans-2,3-disubstituted piperidine derivatives. Chiral substrates were synthesized by Sharpless asymmetric dihydroxylation of the enamine; the antimalarial compound febrifugine was synthesized from the major product of the conjugate addition reaction.
| Original language | English |
|---|---|
| Article number | F10608SS |
| Pages (from-to) | 3081-3087 |
| Number of pages | 7 |
| Journal | Synthesis |
| Issue number | 19 |
| DOIs | |
| Publication status | Published - Oct 1 2008 |
Keywords
- Asymmetric synthesis
- Febrifugine
- Intramolecular conjugate addition
- Lewis acid
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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Sukemoto, S., Oshige, M., Sato, M., Mimura, K. I., Nishioka, H., Abe, H., Harayama, T., & Takeuchi, Y. (2008). Concise asymmetric synthesis of (+)-febrifugine utilizing trans-selective intramolecular conjugate addition. Synthesis, (19), 3081-3087. [F10608SS]. https://doi.org/10.1055/s-2008-1067271