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

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Alkenes
Olefins
Transition metals
HIV-1
Metals
dicyanmethane
hypoiodous acid

Keywords

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

ASJC Scopus subject areas

  • Medicine(all)

Cite this

Hypoiodite-mediated cyclopropanation of alkenes. / Yoshimura, Akira; Koski, Steven R.; Kastern, Brent J.; Fuchs, Jonathan M.; Jones, T. Nicholas; Yusubova, Roza Y.; Nemykin, Victor N.; Zhdankin, Viktor Vladimirovich.

In: Chemistry (Weinheim an der Bergstrasse, Germany), Vol. 20, No. 20, 12.05.2014, p. 5895-5898.

Research output: Contribution to journalArticle

Yoshimura, Akira ; Koski, Steven R. ; Kastern, Brent J. ; Fuchs, Jonathan M. ; Jones, T. Nicholas ; Yusubova, Roza Y. ; Nemykin, Victor N. ; Zhdankin, Viktor Vladimirovich. / Hypoiodite-mediated cyclopropanation of alkenes. In: Chemistry (Weinheim an der Bergstrasse, Germany). 2014 ; Vol. 20, No. 20. pp. 5895-5898.
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AU - Yusubova, Roza Y.

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