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 Vladimirovich Zhdankin

Research output: Contribution to journalArticle

9 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5895-5898
Number of pages4
JournalChemistry (Weinheim an der Bergstrasse, Germany)
Volume20
Issue number20
DOIs
Publication statusPublished - 12 May 2014

Keywords

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

ASJC Scopus subject areas

  • Medicine(all)

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