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

Author:
Wender, Paul A., Ebner, Christian, Fennell, Brandon D., Inagaki, Fuyuhiko, Schröder, Birte
Source:
Organic letters 2017 v.19 no.21 pp. 5810-5813
ISSN:
1523-7052
Subject:
alkynes, ambient temperature, chemical structure, cycloaddition reactions, ethers, regioselectivity
Abstract:
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.
Agid:
5851279