4.4 Article

Selective Synthesis of 3-Methylene-2,3-dihydrofurans or 1,2,4-Trisubstituted Furans via Tandem Reactions of Allenic Ketones with α-Chloro β-Keto Esters or Ketones

Journal

SYNLETT
Volume 25, Issue 5, Pages 687-692

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1340671

Keywords

allenic ketones; furan derivatives; phosphine catalysis; tandem reactions

Funding

  1. National Natural Science Foundation of China [21172057, 21272058, 21307028]
  2. Postdoctoral Science Foundation of Henan Province [2012058]
  3. STRPHP [14A150048]
  4. RFDP [20114104110005]
  5. PCSIRT [IRT 1061]
  6. BCTRP [132300410293]

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Novel and efficient synthesis of functionalized furan derivatives have been developed in this paper. Promoted by K2CO3, allenic ketones underwent tandem reactions with 2-chloroacetoacetate or 3-chloropentane-2,4-dione to afford 3-methylene-2,3-dihydrofurans with high efficiency under remarkably mild conditions. When the same substrates were treated with potassium carbonate and triphenylphosphine, on the other hand, 1,2,4-trisubstituted furans could be obtained in good yields.

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