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Ynol Ethers as Ketene Equivalents in Rhodium-Catalyzed Intermolecular [5 + 2] Cycloaddition Reactions

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2017

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Wender, Paul A.
Ebner, Christian
Fennell, Brandon D.
Inagaki, Fuyuhiko

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https://doi.org/10.1021/acs.orglett.7b02765
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Organic Letters. 2017, 19(21), pp. 5810-5813. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.7b02765

Zusammenfassung

The previously unexplored metal-catalyzed [5 + 2] cycloadditions of vinylcyclopropanes (VCPs) and electron-rich alkynes (ynol ethers) have been found to provide a highly efficient, direct route to dioxygenated seven-membered rings, a common feature of numerous natural and non-natural targets and building blocks for synthesis. The reactions proceed in high yield at room temperature and tolerate a broad range of functionalities. Substituted VCPs were found to react with high regioselectivity.

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ISO 690WENDER, Paul A., Christian EBNER, Brandon D. FENNELL, Fuyuhiko INAGAKI, Birte SCHRÖDER, 2017. Ynol Ethers as Ketene Equivalents in Rhodium-Catalyzed Intermolecular [5 + 2] Cycloaddition Reactions. In: Organic Letters. 2017, 19(21), pp. 5810-5813. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.7b02765
BibTex
@article{Wender2017-11-03Ether-40897,
  year={2017},
  doi={10.1021/acs.orglett.7b02765},
  title={Ynol Ethers as Ketene Equivalents in Rhodium-Catalyzed Intermolecular [5 + 2] Cycloaddition Reactions},
  number={21},
  volume={19},
  issn={1523-7060},
  journal={Organic Letters},
  pages={5810--5813},
  author={Wender, Paul A. and Ebner, Christian and Fennell, Brandon D. and Inagaki, Fuyuhiko and Schröder, Birte}
}
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