Gold(I)-Catalyzed Intermolecular Cyclopropanation of Enynes with Alkenes: Trapping of Two Different Gold Carbenes

Caught in a trap: Intermolecular cyclopropanation reactions of enynes with alkenes allows the synthesis of complex cyclic systems with gold(I) catalysts under mild conditions. Furthermore, gold carbenes are trapped intermolecularly with alkenes (see scheme; L=ligand), thereby providing experimental...

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Published inAngewandte Chemie (International ed.) Vol. 45; no. 36; pp. 6029 - 6032
Main Authors López, Salomé, Herrero-Gómez, Elena, Pérez-Galán, Patricia, Nieto-Oberhuber, Cristina, Echavarren, Antonio M.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 11.09.2006
WILEY‐VCH Verlag
Wiley
Subjects
Alkenes - chemical synthesis
Alkenes - chemistry
Alkynes - chemical synthesis
Alkynes - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cyclization
cyclopropanation
Cyclopropanes - chemistry
enynes
gold
Gold - chemistry
Hydrocarbons - chemistry
Methane - analogs & derivatives
Methane - chemistry
Physical Sciences
rearrangement
Science & Technology
Stereoisomerism
HYDROXYCYCLIZATION
ALKOXYCYCLIZATION
ALKYNYL
PLATINUM
CLOSING METATHESIS
enynes
RUTHENIUM-CATALYZED CYCLOPROPANATION
cyclization
gold
(2-FURYL)CARBENE COMPLEXES
cyclopropanation
CYCLOISOMERIZATION
rearrangement
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Summary:Caught in a trap: Intermolecular cyclopropanation reactions of enynes with alkenes allows the synthesis of complex cyclic systems with gold(I) catalysts under mild conditions. Furthermore, gold carbenes are trapped intermolecularly with alkenes (see scheme; L=ligand), thereby providing experimental evidence for the involvement of two different types of metal carbenes in the skeletal rearrangement of enynes.
Bibliography:AGAUR - No. 2005 SGR 00993
istex:F6186789B82B4E20B243F16197FEBC2AD62E0C83
We are grateful to the MEC (project CTQ2004-02869, Torres Quevedo (contract to S.L. and predoctoral fellowships to E.H.-G., P.P.-G., and C.N.-O.), the AGAUR (2005 SGR 00993), and the ICIQ Foundation for financial support.
MEC - No. CTQ2004-02869
ArticleID:ANIE200602448
ark:/67375/WNG-2M90F0CN-K
ICIQ Foundation
We are grateful to the MEC (project CTQ2004‐02869, Torres Quevedo (contract to S.L. and predoctoral fellowships to E.H.‐G., P.P.‐G., and C.N.‐O.), the AGAUR (2005 SGR 00993), and the ICIQ Foundation for financial support.
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SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200602448