4.6 Article

Mutual Cooperation in the Formal Allyl Alcohol Nucleophilic Substitution and Hydration of Alkynes for the Construction of -Substituted Ketones

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 19, Pages 6458-6465

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600248

Keywords

1; 5-enynols; cyclization; gold catalysis; hydration; nucleophilic substitution; ring-opening reactions

Funding

  1. National Natural Science Foundation of China [21372120, 21202084]
  2. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)

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Mutual cooperation in the formal allyl alcohol nucleophilic substitution reaction and hydration of an alkyne has been utilized in the presence of a gold catalyst to give a series of -functionalized ketones with high to excellent yields. This reaction actually involved an intramolecular O-H insertion cyclization of an alkyne to form the dihydrofuran intermediate, which was followed by the nucleophilic addition ring-opening of a dihydrofuran to give the target compound.

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