Chemistry - A European Journal, volume 19, issue 10, pages 3415-3425

Ni‐Catalyzed [4+3+2] Cycloaddition of Ethyl Cyclopropylideneacetate and Dienynes: Scope and Mechanistic Insights

Ryu Yamasaki ^{1, 2}

Masato Ohashi ³

Kyotaro Maeda ¹

Takuya Kitamura ¹

Minami Nakagawa ¹

Korehito Kato ¹

Tetsushi Fujita ¹

Ryohei Kamura ³

Kazuto KINOSHITA ³

Hyuma Masu ^{4, 5}

Isao Azumaya ⁴

Sensuke Ogoshi ³

Shinichi Saito ¹

Hide authors affiliations Show authors affiliations: 5 affiliations

Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162‐8601 (Japan), Fax: (+81) 3‐5261‐4631 |

Present Address: Molecular Engineering Institute (MEI), Kinki University, 11‐6 Kayanomori, Iizuka, Fukuoka 820‐8555 (Japan) |

Graduate School of Engineering, Osaka University, Suita, Osaka 565‐0871 (Japan), Fax: (+81) 6‐6879‐7394 |

⁴

Faculty of Pharmaceutical Science at Kagawa Campus, Tokushima Bunri University, 1314‐1 Shido, Sanuki, Kagawa 769‐2193 (Japan) |

⁵

Present Address: Chemical Analysis Center, Chiba University, 1‐33 Yayoi‐cho, Inage, Chiba 263‐8522 (Japan) |

Publication type: Journal Article

Publication date: 2013-01-25

Wiley

Journal: Chemistry - A European Journal

Quartile SCImago

Quartile WOS

Impact factor: 4.3

ISSN: 09476539, 15213765

DOI: 10.1002/chem.201204087

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General Chemistry

Catalysis

Organic Chemistry

Abstract

A detailed study of the Ni-catalyzed [4+3+2] cycloaddition reaction between ethyl cyclopropylideneacetate and dienynes has been conducted, resulting in the development of a new method for the synthesis of compounds containing nine-membered rings. We studied the reactivity of various dienynes, together with their substituent and conformational effects. The mechanism of the reaction was probed by examining the stoichiometric reactions of the Ni complexes and dienynes.

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Citations by journals

	1 2 3 4 5
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 5, 11.11% Advanced Synthesis and Catalysis 5 publications, 11.11%
Organic Letters	Organic Letters, 5, 11.11% Organic Letters 5 publications, 11.11%
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 4, 8.89% Angewandte Chemie - International Edition 4 publications, 8.89%
Angewandte Chemie	Angewandte Chemie, 4, 8.89% Angewandte Chemie 4 publications, 8.89%
Tetrahedron Letters	Tetrahedron Letters, 2, 4.44% Tetrahedron Letters 2 publications, 4.44%
Tetrahedron	Tetrahedron, 2, 4.44% Tetrahedron 2 publications, 4.44%
Chemistry - A European Journal	Chemistry - A European Journal, 2, 4.44% Chemistry - A European Journal 2 publications, 4.44%
Chemical Reviews	Chemical Reviews, 2, 4.44% Chemical Reviews 2 publications, 4.44%
Journal of Organic Chemistry	Journal of Organic Chemistry, 2, 4.44% Journal of Organic Chemistry 2 publications, 4.44%
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 2, 4.44% Organic Chemistry Frontiers 2 publications, 4.44%
Molecules	Molecules, 1, 2.22% Molecules 1 publication, 2.22%
Journal of the American Chemical Society	Journal of the American Chemical Society, 1, 2.22% Journal of the American Chemical Society 1 publication, 2.22%
Organometallics	Organometallics, 1, 2.22% Organometallics 1 publication, 2.22%
ACS Catalysis	ACS Catalysis, 1, 2.22% ACS Catalysis 1 publication, 2.22%
Chemical Communications	Chemical Communications, 1, 2.22% Chemical Communications 1 publication, 2.22%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 1, 2.22% Organic and Biomolecular Chemistry 1 publication, 2.22%
Topics in Current Chemistry	Topics in Current Chemistry, 1, 2.22% Topics in Current Chemistry 1 publication, 2.22%
Organic Reaction Mechanisms	Organic Reaction Mechanisms, 1, 2.22% Organic Reaction Mechanisms 1 publication, 2.22%
Synthesis	Synthesis, 1, 2.22% Synthesis 1 publication, 2.22%
Zeitschrift fur Physikalische Chemie	Zeitschrift fur Physikalische Chemie, 1, 2.22% Zeitschrift fur Physikalische Chemie 1 publication, 2.22%
Russian Chemical Reviews	Russian Chemical Reviews, 1, 2.22% Russian Chemical Reviews 1 publication, 2.22%
	1 2 3 4 5

Citations by publishers

	2 4 6 8 10 12 14 16 18 20
Wiley	Wiley, 19, 42.22% Wiley 19 publications, 42.22%
American Chemical Society (ACS)	American Chemical Society (ACS), 12, 26.67% American Chemical Society (ACS) 12 publications, 26.67%
Elsevier	Elsevier, 4, 8.89% Elsevier 4 publications, 8.89%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 4, 8.89% Royal Society of Chemistry (RSC) 4 publications, 8.89%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 1, 2.22% Multidisciplinary Digital Publishing Institute (MDPI) 1 publication, 2.22%
Springer Nature	Springer Nature, 1, 2.22% Springer Nature 1 publication, 2.22%
Thieme	Thieme, 1, 2.22% Thieme 1 publication, 2.22%
Walter de Gruyter	Walter de Gruyter, 1, 2.22% Walter de Gruyter 1 publication, 2.22%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 2.22% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 2.22%
	2 4 6 8 10 12 14 16 18 20

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GOST Copy

Yamasaki R. et al. Ni‐Catalyzed [4+3+2] Cycloaddition of Ethyl Cyclopropylideneacetate and Dienynes: Scope and Mechanistic Insights // Chemistry - A European Journal. 2013. Vol. 19. No. 10. pp. 3415-3425.

GOST all authors (up to 50) Copy

Yamasaki R., Ohashi M., Maeda K., Kitamura T., Nakagawa M., Kato K., Fujita T., Kamura R., KINOSHITA K., Masu H., Azumaya I., Ogoshi S., Saito S. Ni‐Catalyzed [4+3+2] Cycloaddition of Ethyl Cyclopropylideneacetate and Dienynes: Scope and Mechanistic Insights // Chemistry - A European Journal. 2013. Vol. 19. No. 10. pp. 3415-3425.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1002/chem.201204087

UR - https://doi.org/10.1002/chem.201204087

TI - Ni‐Catalyzed [4+3+2] Cycloaddition of Ethyl Cyclopropylideneacetate and Dienynes: Scope and Mechanistic Insights

T2 - Chemistry - A European Journal

AU - Yamasaki, Ryu

AU - Ohashi, Masato

AU - Maeda, Kyotaro

AU - Kitamura, Takuya

AU - Nakagawa, Minami

AU - Kato, Korehito

AU - Fujita, Tetsushi

AU - Kamura, Ryohei

AU - KINOSHITA, Kazuto

AU - Masu, Hyuma

AU - Azumaya, Isao

AU - Ogoshi, Sensuke

AU - Saito, Shinichi

PY - 2013

DA - 2013/01/25 00:00:00

PB - Wiley

SP - 3415-3425

IS - 10

VL - 19

SN - 0947-6539

SN - 1521-3765

ER -

BibTex |

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BibTex Copy

@article{2013_Yamasaki,

author = {Ryu Yamasaki and Masato Ohashi and Kyotaro Maeda and Takuya Kitamura and Minami Nakagawa and Korehito Kato and Tetsushi Fujita and Ryohei Kamura and Kazuto KINOSHITA and Hyuma Masu and Isao Azumaya and Sensuke Ogoshi and Shinichi Saito},

title = {Ni‐Catalyzed [4+3+2] Cycloaddition of Ethyl Cyclopropylideneacetate and Dienynes: Scope and Mechanistic Insights},

journal = {Chemistry - A European Journal},

year = {2013},

volume = {19},

publisher = {Wiley},

month = {jan},

url = {https://doi.org/10.1002/chem.201204087},

number = {10},

pages = {3415--3425},

doi = {10.1002/chem.201204087}

}

MLA

Cite this

MLA Copy

Yamasaki, Ryu, et al. “Ni‐Catalyzed [4+3+2] Cycloaddition of Ethyl Cyclopropylideneacetate and Dienynes: Scope and Mechanistic Insights.” Chemistry - A European Journal, vol. 19, no. 10, Jan. 2013, pp. 3415-3425. https://doi.org/10.1002/chem.201204087.

Found error?

Publisher

Wiley

Journal

Chemistry - A European Journal

Quartile SCImago

Quartile WOS

Impact factor

4.3

ISSN

09476539 (Print)
15213765 (Electronic)