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

Research output: Contribution to journal › Article › peer-review

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

Keywords

cyclopropanation reactions
hypoiodous acid
iodine
oxidation
small ring systems

ASJC Scopus subject areas

Medicine(all)

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10.1002/chem.201402372

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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 journal › Article › peer-review

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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 - cyclopropanation reactions

KW - hypoiodous acid

KW - iodine

KW - oxidation

KW - small ring systems

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