4.8 Article

Catalyst-Controlled Chemoselective All-Alkene [2+2+2] and [2+2] Cyclizations of Enamides with Electron-Deficient Alkenes

Journal

ORGANIC LETTERS
Volume 21, Issue 5, Pages 1458-1462

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00209

Keywords

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Funding

  1. National Natural Science Foundation of China (NSFC) [21432011, 21772224]
  2. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  3. Science and Technology Commission of Shanghai Municipality [17JC1401200]
  4. NSFC/RGC Joint Research Scheme [21461162002]
  5. Key Research Program of Frontier Sciences, CAS [QYZDY-SSW-SLH016]
  6. Natural Science Foundation of Shanghai [17ZR1436900]

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In the presence of 4 angstrom MS, both all-alkene [2 + 2 + 2] and [2 + 2] cyclizations of dimethyl methylenemalonate (DMM) with N-sulfonyl enamides were selectively achieved under In(OTf)(3) and Cu(OTf)(2) catalysis, respectively. In(OTf)(3)-catalyzed [4 + 2] cyclization of the sulfonylamidocyclobutanes with another molecule of DMM or other electron-deficient alkenes was also reported.

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