4.8 Article

A New Catalytic Prins Cyclization Leading to Oxa- and Azacycles

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ORGANIC LETTERS
卷 11, 期 2, 页码 357-360

出版社

AMER CHEMICAL SOC
DOI: 10.1021/ol802593u

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资金

  1. Ministerio de Educacion y Ciencia of Spain
  2. European Regional Development Fund [CTQ2005-09074-C02-01/BQU]
  3. FICIC
  4. Spanish MSC ISCIII [RD06/0020/1046]
  5. Canary Islands Government
  6. Spanish MEC

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A new Prins cyclization process that builds up one carbon-carbon bond, one heteroatom-carbon bond, and one halogen-carbon bond, (in an oxa- and azacycle) relies on an iron catalyst system formed from Fe(acac)(3) and trimethylsilyl halide. The method displays a broad substrate scope and is economical, environmentally friendly, and experimentally simple. This catalytic method permits the construction of chloro, bromo and iodo heterocycles, by the suitable combination of iron(III) source, the corresponding trimethylsilyl halide and the solvent, in high yields.

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