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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 V Zhdankin

CHEMISTRY-A EUROPEAN JOURNAL（2014）

Cited 14|Views8
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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.
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Key words
cyclopropanation reactions,hypoiodous acid,iodine,oxidation,small ring systems
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