Gold(I)-catalyzed Claisen rearrangement of allenyl vinyl ethers; synthesis of substituted 1,3-dienes |
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| Authors: | Krafft Marie E Hallal Kassem M Vidhani Dinesh V Cran John W |
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| Affiliation: | Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA. mek@chem.fsu.edu |
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| Abstract: | Synthesis of substituted 1,3-dienes was achieved via gold(I)-catalyzed Claisen rearrangement of allenyl vinyl ethers. The N-heterocyclic carbene gold 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. |
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