Stereospecific Decarboxylative Nazarov Cyclization Mediated by Carbon Dioxide for the Preparation of Highly Substituted 2‐Cyclopentenones

• DOI: 10.1002/anie.201705909
• Publication Date: 2017-07-20T12:12:49Z
• Authors: Keiichi Komatsuki; Yuta Sadamitsu; Kohei Sekine; Kodai Saito; Tohru Yamada
• Keywords: Cyclopentenone; Stereospecificity; Propargyl; Decarboxylation; Derivative (finance); Alkene

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 propargyl alcohol carbon dioxide in presence a silver catalyst. The stereochemistry 2‐cyclopentenone strictly controlled geometry alkene starting material. This method applicable for various substrates.