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Stereospecific Decarboxylative Nazarov Cyclization Mediated by Carbon Dioxide for the Preparation of Highly Substituted 2‐Cyclopentenones
Author(s) -
Komatsuki Keiichi,
Sadamitsu Yuta,
Sekine Kohei,
Saito Kodai,
Yamada Tohru
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201705909
Subject(s) - chemistry , catalysis , cyclopentenone , stereospecificity , propargyl , carbon dioxide , lewis acids and bases , decarboxylation , derivative (finance) , alkene , organic chemistry , carboxylation , medicinal chemistry , financial economics , economics
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.