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

Keiichi Komatsuki; Yuta Sadamitsu; Kohei Sekine; Kodai Saito; Tohru Yamada

doi:10.1002/anie.201705909

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

Keiichi Komatsuki, Yuta Sadamitsu, Kohei Sekine, Kodai Saito, Tohru Yamada

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

26 Citations (Scopus)

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	https://doi.org/10.1002/anie.201705909
Publication status	Published - 2017 Sep 11

Keywords

C−C bond formation
carbon dioxide
electrocyclic reactions
silver
stereospecific reactions

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201705909

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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 › peer-review

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keywords = "C−C bond formation, carbon dioxide, electrocyclic reactions, silver, stereospecific reactions",

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AU - Sekine, Kohei

AU - Saito, Kodai

AU - Yamada, Tohru

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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.

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KW - electrocyclic reactions

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KW - stereospecific reactions

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

Abstract

Keywords

ASJC Scopus subject areas

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