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Issue 21, 2011
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Gold(I)-catalyzed Claisen rearrangement of allenyl vinyl ethers; synthesis of substituted 1,3-dienes

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Abstract

Synthesis of substituted 1,3-dienes was achieved viagold(I)-catalyzed Claisen rearrangement of allenyl vinyl ethers. The N-heterocyclic carbenegold chloride catalyst (IPrAuCl) was superior in terms of activity and selectivity and afforded the 3,3-product in excellent yields. A proposed cation-π inter-action played a significant role in affecting the reaction rate.

Graphical abstract: Gold(i)-catalyzed Claisen rearrangement of allenyl vinyl ethers; synthesis of substituted 1,3-dienes

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The article was received on 09 Jun 2011, accepted on 09 Aug 2011 and first published on 10 Aug 2011


Article type: Paper
DOI: 10.1039/C1OB06297B
Citation: Org. Biomol. Chem., 2011,9, 7535-7538
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    Gold(I)-catalyzed Claisen rearrangement of allenyl vinyl ethers; synthesis of substituted 1,3-dienes

    M. E. Krafft, K. M. Hallal, D. V. Vidhani and J. W. Cran, Org. Biomol. Chem., 2011, 9, 7535
    DOI: 10.1039/C1OB06297B

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