Hypoiodite-Mediated Cyclopropanation of Alkenes
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.
Yoshimura, A.*; Koski, S. R.; Kastern, B. J.; Fuchs, J. M.; Jones, T. N.; Yusubova, R. Y.; Nemykin, V. N.; Zhdankin V. V.* Hypoiodite-Mediated Cyclopropanation of Alkenes. Chem. Eur. J., 2014, 20, 5895-5898.