Abstract
An enantiocontrolled total synthesis of 19,20-dihydroakuammicine using a catalytic asymmetric MiChael addition of dimethyl malonate to cyclohexenone as the key step is described. The above catalytic asymmetric Michael addition proceeds quite efficiently in the presence of a heterobimetalic asymmetric catalyst (ALB-KO-t-Bu-MS 4A, 0.3 mol%), giving the corresponding Michael adduct in 94% yield and 99% ee. (C) 2000 Wiley-Liss, Inc.
| Original language | English |
|---|---|
| Pages (from-to) | 400-403 |
| Number of pages | 4 |
| Journal | Chirality |
| Volume | 12 |
| Issue number | 5-6 |
| Publication status | Published - Jan 1 2000 |
| Externally published | Yes |
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All Science Journal Classification (ASJC) codes
- Analytical Chemistry
- Catalysis
- Pharmacology
- Drug Discovery
- Spectroscopy
- Organic Chemistry
Cite this
Catalytic asymmetric synthesis of 19,20-dihydroakuammicine. / Ohori, Ken; Shimizu, Satoshi; Ohshima, Takashi; Shibasaki, Masakatsu.
In: Chirality, Vol. 12, No. 5-6, 01.01.2000, p. 400-403.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Catalytic asymmetric synthesis of 19,20-dihydroakuammicine
AU - Ohori, Ken
AU - Shimizu, Satoshi
AU - Ohshima, Takashi
AU - Shibasaki, Masakatsu
PY - 2000/1/1
Y1 - 2000/1/1
N2 - An enantiocontrolled total synthesis of 19,20-dihydroakuammicine using a catalytic asymmetric MiChael addition of dimethyl malonate to cyclohexenone as the key step is described. The above catalytic asymmetric Michael addition proceeds quite efficiently in the presence of a heterobimetalic asymmetric catalyst (ALB-KO-t-Bu-MS 4A, 0.3 mol%), giving the corresponding Michael adduct in 94% yield and 99% ee. (C) 2000 Wiley-Liss, Inc.
AB - An enantiocontrolled total synthesis of 19,20-dihydroakuammicine using a catalytic asymmetric MiChael addition of dimethyl malonate to cyclohexenone as the key step is described. The above catalytic asymmetric Michael addition proceeds quite efficiently in the presence of a heterobimetalic asymmetric catalyst (ALB-KO-t-Bu-MS 4A, 0.3 mol%), giving the corresponding Michael adduct in 94% yield and 99% ee. (C) 2000 Wiley-Liss, Inc.
UR - http://www.scopus.com/inward/record.url?scp=0034034225&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0034034225&partnerID=8YFLogxK
M3 - Article
C2 - 10824160
AN - SCOPUS:0034034225
VL - 12
SP - 400
EP - 403
JO - Chirality
JF - Chirality
SN - 0899-0042
IS - 5-6
ER -