Cover Picture: Gold(I)-Catalyzed Domino Reaction of Allyl 2-en-4-ynyl Ethers to 1,3,6-Trien-4-yl Ketones (ChemCatChem 5/2013)

Authors

  • Prof. Dr. A. Stephen K. Hashmi,

    Corresponding author
    1. Organisch Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-54-4205
    • Organisch Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-54-4205
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  • Dipl.-Chem. Katharina Graf,

    1. Organisch Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-54-4205
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  • Dr. Martin Ackermann,

    1. Organisch Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-54-4205
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  • Dr. Frank Rominger

    1. Organisch Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-54-4205
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Abstract

original image

Golden metamorphose! The cover picture shows a linear unsaturated molecule, which in the presence of a gold catalyst rearranges to a complicated branched product, an isomerization involving an oxygen atom transfer. This resembles the fascinating metamorphose of a caterpillar to a butterfly. In their Full Paper on p. 1200 ff., A. S. K. Hashmi, K. Graf et al. report that this conversion proceeds in a highly diastereoselective manner. A complex cascade involving activation by π coordination of gold, a [3,3]-sigmatropic rearrangement, and an electrocyclic ring opening is suggested as the mechanism of this conversion.

Cartoon 1.

Ancillary

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