Chemistry - A European Journal, volume 12, issue 2, pages 510-517

Synthesis of the Indene, THF, and Pyrrolidine Skeletons by Lewis Acid Mediated Cycloaddition of Methylenecyclopropanes with Aldehydes,N-Tosyl Aldimines, and Acetals

Li-Xiong Shao ¹

Bo Xu Bo ¹

Jin Wen Huang ¹

Min Shi ²

Hide authors affiliations Show authors affiliations: 2 affiliations

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (China) |

East China University of Science and Technology, 130 Mei Long Lu, Shanghai 200237, China, Fax: (+86) 21‐6416‐6128 |

Publication type: Journal Article

Publication date: 2006-01-01

Wiley

Journal: Chemistry - A European Journal

Quartile SCImago

Quartile WOS

Impact factor: 4.3

ISSN: 09476539, 15213765

DOI: 10.1002/chem.200500447

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General Chemistry

Catalysis

Organic Chemistry

Abstract

Methylenecyclopropanes (MCPs 1) react with aldehydes, N-tosyl aldimines, and acetals to give the corresponding indene, THF, and pyrrolidine cycloaddition products in the presence of BF3 x OEt2 under mild reaction conditions. Some special transformations of MCPs 1 with aldehydes have been reported in this paper. A plausible reaction mechanism has been discussed, which is based on a deuterium-labeling experiment and the Prins-type reaction mechanism.

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European Journal of Organic Chemistry	European Journal of Organic Chemistry, 8, 14.04% European Journal of Organic Chemistry 8 publications, 14.04%
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Chemistry - A European Journal	Chemistry - A European Journal, 5, 8.77% Chemistry - A European Journal 5 publications, 8.77%
Chemical Communications	Chemical Communications, 3, 5.26% Chemical Communications 3 publications, 5.26%
Journal of Organometallic Chemistry	Journal of Organometallic Chemistry, 2, 3.51% Journal of Organometallic Chemistry 2 publications, 3.51%
Tetrahedron Letters	Tetrahedron Letters, 2, 3.51% Tetrahedron Letters 2 publications, 3.51%
Chinese Journal of Chemistry	Chinese Journal of Chemistry, 2, 3.51% Chinese Journal of Chemistry 2 publications, 3.51%
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Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 2, 3.51% Organic and Biomolecular Chemistry 2 publications, 3.51%
ChemistrySelect	ChemistrySelect, 1, 1.75% ChemistrySelect 1 publication, 1.75%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 1, 1.75% Advanced Synthesis and Catalysis 1 publication, 1.75%
ChemInform	ChemInform, 1, 1.75% ChemInform 1 publication, 1.75%
Journal of Organic Chemistry	Journal of Organic Chemistry, 1, 1.75% Journal of Organic Chemistry 1 publication, 1.75%
Organometallics	Organometallics, 1, 1.75% Organometallics 1 publication, 1.75%
Accounts of Chemical Research	Accounts of Chemical Research, 1, 1.75% Accounts of Chemical Research 1 publication, 1.75%
Dalton Transactions	Dalton Transactions, 1, 1.75% Dalton Transactions 1 publication, 1.75%
RSC Advances	RSC Advances, 1, 1.75% RSC Advances 1 publication, 1.75%
Chemical Science	Chemical Science, 1, 1.75% Chemical Science 1 publication, 1.75%
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 1, 1.75% Organic Chemistry Frontiers 1 publication, 1.75%
Synthetic Communications	Synthetic Communications, 1, 1.75% Synthetic Communications 1 publication, 1.75%
Organic Preparations and Procedures International	Organic Preparations and Procedures International, 1, 1.75% Organic Preparations and Procedures International 1 publication, 1.75%
Organic Reaction Mechanisms	Organic Reaction Mechanisms, 1, 1.75% Organic Reaction Mechanisms 1 publication, 1.75%
Synlett	Synlett, 1, 1.75% Synlett 1 publication, 1.75%
Russian Chemical Reviews	Russian Chemical Reviews, 1, 1.75% Russian Chemical Reviews 1 publication, 1.75%
Chemistry - An Asian Journal	Chemistry - An Asian Journal, 1, 1.75% Chemistry - An Asian Journal 1 publication, 1.75%
	1 2 3 4 5 6 7 8

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	5 10 15 20 25
Wiley	Wiley, 22, 38.6% Wiley 22 publications, 38.6%
American Chemical Society (ACS)	American Chemical Society (ACS), 11, 19.3% American Chemical Society (ACS) 11 publications, 19.3%
Elsevier	Elsevier, 9, 15.79% Elsevier 9 publications, 15.79%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 9, 15.79% Royal Society of Chemistry (RSC) 9 publications, 15.79%
Taylor & Francis	Taylor & Francis, 2, 3.51% Taylor & Francis 2 publications, 3.51%
Thieme	Thieme, 1, 1.75% Thieme 1 publication, 1.75%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 1.75% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 1.75%
	5 10 15 20 25

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Shao L. et al. Synthesis of the Indene, THF, and Pyrrolidine Skeletons by Lewis Acid Mediated Cycloaddition of Methylenecyclopropanes with Aldehydes,N-Tosyl Aldimines, and Acetals // Chemistry - A European Journal. 2006. Vol. 12. No. 2. pp. 510-517.

GOST all authors (up to 50) Copy

Shao L., Xu Bo B., Huang J. W., Shi M. Synthesis of the Indene, THF, and Pyrrolidine Skeletons by Lewis Acid Mediated Cycloaddition of Methylenecyclopropanes with Aldehydes,N-Tosyl Aldimines, and Acetals // Chemistry - A European Journal. 2006. Vol. 12. No. 2. pp. 510-517.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1002/chem.200500447

UR - https://doi.org/10.1002/chem.200500447

TI - Synthesis of the Indene, THF, and Pyrrolidine Skeletons by Lewis Acid Mediated Cycloaddition of Methylenecyclopropanes with Aldehydes,N-Tosyl Aldimines, and Acetals

T2 - Chemistry - A European Journal

AU - Shao, Li-Xiong

AU - Xu Bo, Bo

AU - Huang, Jin Wen

AU - Shi, Min

PY - 2006

DA - 2006/01/01 00:00:00

PB - Wiley

SP - 510-517

IS - 2

VL - 12

SN - 0947-6539

SN - 1521-3765

ER -

BibTex |

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BibTex Copy

@article{2006_Shao,

author = {Li-Xiong Shao and Bo Xu Bo and Jin Wen Huang and Min Shi},

title = {Synthesis of the Indene, THF, and Pyrrolidine Skeletons by Lewis Acid Mediated Cycloaddition of Methylenecyclopropanes with Aldehydes,N-Tosyl Aldimines, and Acetals},

journal = {Chemistry - A European Journal},

year = {2006},

volume = {12},

publisher = {Wiley},

month = {jan},

url = {https://doi.org/10.1002/chem.200500447},

number = {2},

pages = {510--517},

doi = {10.1002/chem.200500447}

}

MLA

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MLA Copy

Shao, Li-Xiong, et al. “Synthesis of the Indene, THF, and Pyrrolidine Skeletons by Lewis Acid Mediated Cycloaddition of Methylenecyclopropanes with Aldehydes,N-Tosyl Aldimines, and Acetals.” Chemistry - A European Journal, vol. 12, no. 2, Jan. 2006, pp. 510-517. https://doi.org/10.1002/chem.200500447.

Found error?

Publisher

Wiley

Journal

Chemistry - A European Journal

Quartile SCImago

Quartile WOS

Impact factor

4.3

ISSN

09476539 (Print)
15213765 (Electronic)