Tetrahedron

, volume 63 , issue 40 , pages 9979-9990

Cycloisomerization of γ- and δ-acetylenic acids catalyzed by gold(I) chloride

Estelle Marchal ¹

P. Uriac ¹

Béatrice Legouin ¹

Loïc Toupet ²

Pierre Van De Weghe ^{1, 3}

Hide authors affiliations Show authors affiliations: 3 affiliations

EA Substances Lichéniques et Photoprotection, Faculté de Pharmacie, Université de Rennes 1, avenue du Prof. L. Bernard, F-35043 Rennes Cedex, France |

GMCM, CNRS, UMR 6509, Université de Rennes 1, Campus de Beaulieu, F-35042 Rennes Cedex, France |

Laboratoire de Chimie Organique et Bioorganique associé au CNRS UMR 7015, ENSC-Mu, Université de Haute Alsace, 3, rue A. Werner, F-68093 Mulhouse, France |

Publication type: Journal Article

Publication date: 2007-10-01

Elsevier

Tetrahedron

scimago Q3

wos Q2

SJR: 0.426

CiteScore: 4.1

Impact factor: 2.2

ISSN: 00404020, 14645416

DOI: 10.1016/j.tet.2007.07.066

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Organic Chemistry

Drug Discovery

Biochemistry

Abstract

We have developed a gold(I)-catalyzed intramolecular cyclization of γ- and δ-alkyne acids in mild conditions yielding various alkylidene lactones. Whereas a slight electronic effect of the R group was observed on the regioselectivity, bulky substituents on the R group bearing the alkyne strongly modify the reactivity. The cycloisomerization of o -alkynylbenzoic methyl esters was achieved rather with AuCl 3 as catalyst owing the presence of water affording exclusively the isocoumarins.

Found

1 citation

Loginov Dmitry

🥼

DSc in Chemistry

126 publications, 1 794 citations, 36 reviews

h-index: 25

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

Research interests

Catalysis

Coordination Chemistry

Organic Chemistry

Organic synthesis

Organometallic Chemistry

Photonics

1 citation

Arsenov Mikhail

13 publications, 125 citations

h-index: 7

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

Research interests

Asymmetric metal complex catalysis

Catalysis

Organic Chemistry

Organoelement chemistry

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GOST |

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GOST Copy

Marchal E. et al. Cycloisomerization of γ- and δ-acetylenic acids catalyzed by gold(I) chloride // Tetrahedron. 2007. Vol. 63. No. 40. pp. 9979-9990.

GOST all authors (up to 50) Copy

Marchal E., Uriac P., Legouin B., Toupet L., Weghe P. V. D. Cycloisomerization of γ- and δ-acetylenic acids catalyzed by gold(I) chloride // Tetrahedron. 2007. Vol. 63. No. 40. pp. 9979-9990.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/j.tet.2007.07.066

UR - https://doi.org/10.1016/j.tet.2007.07.066

TI - Cycloisomerization of γ- and δ-acetylenic acids catalyzed by gold(I) chloride

T2 - Tetrahedron

AU - Marchal, Estelle

AU - Uriac, P.

AU - Legouin, Béatrice

AU - Toupet, Loïc

AU - Weghe, Pierre Van De

PY - 2007

DA - 2007/10/01

PB - Elsevier

SP - 9979-9990

IS - 40

VL - 63

SN - 0040-4020

SN - 1464-5416

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2007_Marchal,

author = {Estelle Marchal and P. Uriac and Béatrice Legouin and Loïc Toupet and Pierre Van De Weghe},

title = {Cycloisomerization of γ- and δ-acetylenic acids catalyzed by gold(I) chloride},

journal = {Tetrahedron},

year = {2007},

volume = {63},

publisher = {Elsevier},

month = {oct},

url = {https://doi.org/10.1016/j.tet.2007.07.066},

number = {40},

pages = {9979--9990},

doi = {10.1016/j.tet.2007.07.066}

}

MLA

Cite this

MLA Copy

Marchal, Estelle, et al. “Cycloisomerization of γ- and δ-acetylenic acids catalyzed by gold(I) chloride.” Tetrahedron, vol. 63, no. 40, Oct. 2007, pp. 9979-9990. https://doi.org/10.1016/j.tet.2007.07.066.

Publisher

Elsevier

Journal

Tetrahedron

scimago Q3

wos Q2

SJR

0.426

CiteScore

4.1

Impact factor

2.2

ISSN

00404020 (Print)

14645416 (Electronic)