, 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

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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

Chemistry - A European Journal

scimago Q1

wos Q2

SJR: 0.981

CiteScore: 6.7

Impact factor: 3.7

ISSN: 09476539, 15213765

DOI: 10.1002/chem.200500447

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PubMed ID: 16163769

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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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 |

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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

PB - Wiley

SP - 510-517

IS - 2

VL - 12

PMID - 16163769

SN - 0947-6539

SN - 1521-3765

ER -

BibTex |

Cite this

BibTex (up to 50 authors) 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.

Publisher

Wiley

Journal

Chemistry - A European Journal

scimago Q1

wos Q2

SJR

0.981

CiteScore

6.7

Impact factor

3.7

ISSN

09476539 (Print)

15213765 (Electronic)