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 |
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Keywords
- Asymmetric synthesis
- Febrifugine
- Intramolecular conjugate addition
- Lewis acid
ASJC Scopus subject areas
- Organic Chemistry
- Catalysis
Cite this
Concise asymmetric synthesis of (+)-febrifugine utilizing trans-selective intramolecular conjugate addition. / Sukemoto, Satoshi; Oshige, Miyo; Sato, Masahiro; Mimura, Ken Ichiro; Nishioka, Hiromi; Abe, Hitoshi; Harayama, Takashi; Takeuchi, Yasuo.
In: Synthesis, No. 19, F10608SS, 01.10.2008, p. 3081-3087.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Concise asymmetric synthesis of (+)-febrifugine utilizing trans-selective intramolecular conjugate addition
AU - Sukemoto, Satoshi
AU - Oshige, Miyo
AU - Sato, Masahiro
AU - Mimura, Ken Ichiro
AU - Nishioka, Hiromi
AU - Abe, Hitoshi
AU - Harayama, Takashi
AU - Takeuchi, Yasuo
PY - 2008/10/1
Y1 - 2008/10/1
N2 - 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.
AB - 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.
KW - Asymmetric synthesis
KW - Febrifugine
KW - Intramolecular conjugate addition
KW - Lewis acid
UR - http://www.scopus.com/inward/record.url?scp=53949085124&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=53949085124&partnerID=8YFLogxK
U2 - 10.1055/s-2008-1067271
DO - 10.1055/s-2008-1067271
M3 - Article
AN - SCOPUS:53949085124
SP - 3081
EP - 3087
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 19
M1 - F10608SS
ER -