Abstract
Highly substituted 2-cyclopentenones were stereospecifically and regioselectively constructed with high catalytic efficiency through Lewis-acid catalyzed decarboxylative Nazarov cyclization of the cyclic carbonate derivative, which is prepared by reacting the propargyl alcohol with carbon dioxide in the presence of a silver catalyst. The stereochemistry of the 2-cyclopentenone is strictly controlled by the geometry of the alkene in the starting material. This method is applicable for various substrates.
| Original language | English |
|---|---|
| Pages (from-to) | 11594-11598 |
| Number of pages | 5 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 56 |
| Issue number | 38 |
| DOIs | |
| Publication status | Published - 2017 Sep 11 |
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Keywords
- carbon dioxide
- C−C bond formation
- electrocyclic reactions
- silver
- stereospecific reactions
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
Cite this
Stereospecific Decarboxylative Nazarov Cyclization Mediated by Carbon Dioxide for the Preparation of Highly Substituted 2-Cyclopentenones. / Komatsuki, Keiichi; Sadamitsu, Yuta; Sekine, Kohei; Saito, Kodai; Yamada, Tohru.
In: Angewandte Chemie - International Edition, Vol. 56, No. 38, 11.09.2017, p. 11594-11598.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Stereospecific Decarboxylative Nazarov Cyclization Mediated by Carbon Dioxide for the Preparation of Highly Substituted 2-Cyclopentenones
AU - Komatsuki, Keiichi
AU - Sadamitsu, Yuta
AU - Sekine, Kohei
AU - Saito, Kodai
AU - Yamada, Tohru
PY - 2017/9/11
Y1 - 2017/9/11
N2 - Highly substituted 2-cyclopentenones were stereospecifically and regioselectively constructed with high catalytic efficiency through Lewis-acid catalyzed decarboxylative Nazarov cyclization of the cyclic carbonate derivative, which is prepared by reacting the propargyl alcohol with carbon dioxide in the presence of a silver catalyst. The stereochemistry of the 2-cyclopentenone is strictly controlled by the geometry of the alkene in the starting material. This method is applicable for various substrates.
AB - Highly substituted 2-cyclopentenones were stereospecifically and regioselectively constructed with high catalytic efficiency through Lewis-acid catalyzed decarboxylative Nazarov cyclization of the cyclic carbonate derivative, which is prepared by reacting the propargyl alcohol with carbon dioxide in the presence of a silver catalyst. The stereochemistry of the 2-cyclopentenone is strictly controlled by the geometry of the alkene in the starting material. This method is applicable for various substrates.
KW - carbon dioxide
KW - C−C bond formation
KW - electrocyclic reactions
KW - silver
KW - stereospecific reactions
UR - http://www.scopus.com/inward/record.url?scp=85028831860&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85028831860&partnerID=8YFLogxK
U2 - 10.1002/anie.201705909
DO - 10.1002/anie.201705909
M3 - Article
C2 - 28727245
AN - SCOPUS:85028831860
VL - 56
SP - 11594
EP - 11598
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 38
ER -