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

The Kizhner Research Center

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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 language	English
Pages (from-to)	5895-5898
Number of pages	4
Journal	Chemistry (Weinheim an der Bergstrasse, Germany)
Volume	20
Issue number	20
DOIs	https://doi.org/10.1002/chem.201402372
Publication status	Published - 12 May 2014

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Keywords

cyclopropanation reactions
hypoiodous acid
iodine
oxidation
small ring systems

ASJC Scopus subject areas

Medicine(all)

Cite this

Yoshimura, A., Koski, S. R., Kastern, B. J., Fuchs, J. M., Jones, T. N., Yusubova, R. Y., Nemykin, V. N., & Zhdankin, V. V. (2014). Hypoiodite-mediated cyclopropanation of alkenes. Chemistry (Weinheim an der Bergstrasse, Germany), 20(20), 5895-5898. https://doi.org/10.1002/chem.201402372

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AU - Koski, Steven R.

AU - Kastern, Brent J.

AU - Fuchs, Jonathan M.

AU - Jones, T. Nicholas

AU - Yusubova, Roza Y.

AU - Nemykin, Victor N.

AU - Zhdankin, Viktor Vladimirovich

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KW - small ring systems

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10.1002/chem.201402372