A copper-catalyzed domino radical cyclization route to benzospiro-indolizidinepyrrolidinones

Christian V. Stevens, Ellen Van Meenen, Kurt G.R. Masschelein, Yves Eeckhout, Wim Hooghe, Bart D'hondt, Victor N. Nemykin, Viktor Zhdankin

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20 Scopus citations

Abstract

In this Letter the synthesis of benzospiro-indolizidinepyrrolidinones is described by a domino atom transfer radical cyclization reaction using a copper catalyst. The structure of one of the products was established by single crystal X-ray diffraction. The investigated precursors, bearing a homo allyl substituent on the N-indole, result in a 5-exo-trig, followed by a 6-endo-trig cyclization. When the N-indole is substituted with an allyl group, only the spiro-cyclization occurs.

Original languageEnglish (US)
Pages (from-to)7108-7111
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number40
DOIs
StatePublished - Oct 1 2007

Keywords

  • ATRC
  • Atom transfer radical cyclization
  • Cu(I)Cl
  • Domino reaction

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