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
N1 - Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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.
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U2 - 10.1002/anie.201705909
DO - 10.1002/anie.201705909
M3 - Article
C2 - 28727245
AN - SCOPUS:85028831860
SN - 1433-7851
VL - 56
SP - 11594
EP - 11598
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 38
ER -