4.7 Article

TBAF-Catalyzed O-Nucleophilic Cyclization of Enaminones: A Process for the Synthesis of Dihydroisobenzofuran Derivatives

期刊

JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 3, 页码 1379-1386

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02842

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资金

  1. Shandong Natural Science Foundation [ZR2018BB026, ZR2018JL013]
  2. National Natural Science Foundation of China [21475075]
  3. Doctoral Start-Up Scientific Research Foundation of Qufu Normal University

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A novel methodology for the stereoselective synthesis of dihydroisobenzofuran derivatives is described in this paper. The procedure was realized by the bifunctional TBAF catalyzed selective O-nucleophilic cyclization of enaminone with intramolecular alkyne under mild and non-metal-mediated conditions. The results of control experiments suggested that the cation-pi interaction and basicity, offered by TBAF, might be indispensable for the isomerization of enaminone and the formation of carbon-oxygen bond.

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