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

doi:10.1002/chem.201402372

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

Chemistry & Biochemistry

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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 language	English (US)
Pages (from-to)	5895-5898
Number of pages	4
Journal	Chemistry - A European Journal
Volume	20
Issue number	20
DOIs	https://doi.org/10.1002/chem.201402372
State	Published - May 12 2014

Keywords

cyclopropanation reactions
hypoiodous acid
iodine
oxidation
small ring systems

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title = "Hypoiodite-mediated cyclopropanation of alkenes",

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).",

keywords = "cyclopropanation reactions, hypoiodous acid, iodine, oxidation, small ring systems",

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

year = "2014",

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doi = "10.1002/chem.201402372",

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AU - Yoshimura, Akira

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

PY - 2014/5/12

Y1 - 2014/5/12

N2 - 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).

AB - 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).

KW - cyclopropanation reactions

KW - hypoiodous acid

KW - iodine

KW - oxidation

KW - small ring systems

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DO - 10.1002/chem.201402372

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EP - 5898

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

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ER -

Hypoiodite-mediated cyclopropanation of alkenes

Abstract

Keywords

UN SDGs

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