4.5 Article

A Cobalt-Catalyzed Multicomponent Approach to Novel 2,3-Di- and 2,2,3-Trisubstituted 3-Methoxycarbonyl-gamma-butyrolactones

期刊

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2010, 期 27, 页码 5279-5286

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000698

关键词

Lactones; Multicomponent reactions; Domino reactions; Cobalt; Zinc

资金

  1. Centre National de la Recherche Scientifique (CNRS)
  2. University Paris Est Creteil

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A one-pot, three-component synthesis of the title butyrolactones starting from aryl bromides, dimethyl itaconate, and either aldehydes or ketones is described. The cobalt-catalyzed domino process formally involves the in situ metalation of an aromatic bromide, conjugate addition onto dimethyl itaconate, an aldolization reaction with a carbonyl compound and a final cyclization into a five-membered lactone. This procedure is applied to the concise synthesis of a range of functionalized gamma-butyrolactones with a methyl paraconate subunit.

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