Issue 21, 2011
From the journal:

Organic & Biomolecular Chemistry

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

Marie E. Krafft,*a   Kassem M. Hallal,a   Dinesh V. Vidhania  and  John W. Crana  

* Corresponding authors

a Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL, USA
E-mail: mek@chem.fsu.edu
Fax: +1 850-644-7409
Tel: +1 850-644-2297

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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Article information

DOI
https://doi.org/10.1039/C1OB06297B
Article type
Paper
Submitted
09 Jun 2011
Accepted
09 Aug 2011
First published
10 Aug 2011

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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