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

43 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 Sept 11

Keywords

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

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1002/anie.201705909

Cite this

@article{4d4656bb7cb94cd5919ba05b9cf15fe4,

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

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.",

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

author = "Keiichi Komatsuki and Yuta Sadamitsu and Kohei Sekine and Kodai Saito and Tohru Yamada",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

month = sep,

day = "11",

doi = "10.1002/anie.201705909",

language = "English",

volume = "56",

pages = "11594--11598",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "38",

}

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 - C−C bond formation

KW - carbon dioxide

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

SN - 1433-7851

VL - 56

SP - 11594

EP - 11598

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 38

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this