Hypoiodite-mediated cyclopropanation of alkenes

Akira Yoshimura, Steven R. Koski, Brent J. Kastern, Jonathan M. Fuchs, T. Nicholas Jones, Roza Y. Yusubova, Victor N. Nemykin, Viktor Zhdankin

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

An efficient, transition metal-free procedure for the cyclopropanation of alkenes using malononitrile and the LiI-tBuOCl combination under mild reaction conditions is described. The reaction mechanism most likely involves tBuOI generated in situ from LiI and tBuOCl. The utility of this new methodology has been demonstrated by the synthesis of a potential HIV-1 RT inhibitor. An efficient, transition-metal-free procedure for the cyclopropanation of alkenes using malononitrile and the LiI/tBuOCl combination under mild reaction conditions is described. The reaction mechanism most likely involves tBuOI generated in situ from LiI and tBuOCl. The utility of this new methodology has been demonstrated by the synthesis of a potential HIV-1 RT inhibitor (see scheme).

Original languageEnglish (US)
Pages (from-to)5895-5898
Number of pages4
JournalChemistry - A European Journal
Volume20
Issue number20
DOIs
StatePublished - May 12 2014

Keywords

  • cyclopropanation reactions
  • hypoiodous acid
  • iodine
  • oxidation
  • small ring systems

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