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 |
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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