4.5 Article

Asymmetric Diastereoselective Synthesis of Spirocyclopropane Derivatives of Oxindole

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 17, Pages 3599-3606

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201402061

Keywords

Organocatalysis; Asymmetric synthesis; Cyclization; Michael addition; Small ring systems

Funding

  1. Estonian Ministry of Education and Research [IUT 19-32]
  2. EU European Regional Development Fund [3.2.0101.08-0017]

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A new asymmetric organocatalytic synthesis of spirocyclopropane oxindoles has been developed. The method is based on the Michael addition of N-Boc-protected 3-chlorooxindole to unsaturated 1,4-dicarbonyl compounds, affording trans-substituted spirocyclopropane oxindole derivatives in high diastereo- and enantioselectivity.

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