Abstract
Hydrolytic enantioselective protonation of dienyl esters and a β-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active α,β-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er).
| Original language | English |
|---|---|
| Pages (from-to) | 6178-6181 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 14 |
| Issue number | 24 |
| DOIs | |
| Publication status | Published - Dec 21 2012 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Hydrolytic enantioselective protonation of cyclic dienyl esters and a β-diketone with chiral phase-transfer catalysts. / Yamamoto, Eiji; Gokuden, Daichi; Nagai, Ayano; Kamachi, Takashi; Yoshizawa, Kazunari; Hamasaki, Akiyuki; Ishida, Tamao; Tokunaga, Makoto.
In: Organic Letters, Vol. 14, No. 24, 21.12.2012, p. 6178-6181.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Hydrolytic enantioselective protonation of cyclic dienyl esters and a β-diketone with chiral phase-transfer catalysts
AU - Yamamoto, Eiji
AU - Gokuden, Daichi
AU - Nagai, Ayano
AU - Kamachi, Takashi
AU - Yoshizawa, Kazunari
AU - Hamasaki, Akiyuki
AU - Ishida, Tamao
AU - Tokunaga, Makoto
PY - 2012/12/21
Y1 - 2012/12/21
N2 - Hydrolytic enantioselective protonation of dienyl esters and a β-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active α,β-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er).
AB - Hydrolytic enantioselective protonation of dienyl esters and a β-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active α,β-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er).
UR - http://www.scopus.com/inward/record.url?scp=84871551069&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84871551069&partnerID=8YFLogxK
U2 - 10.1021/ol3027363
DO - 10.1021/ol3027363
M3 - Article
C2 - 23205886
AN - SCOPUS:84871551069
VL - 14
SP - 6178
EP - 6181
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 24
ER -