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Hypoiodite‐Mediated Cyclopropanation of Alkenes |
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| Authors: | Dr Akira Yoshimura Steven R Koski Brent J Kastern Jonathan M Fuchs Prof Dr T Nicholas Jones Dr Roza Y Yusubova Prof Dr Victor N Nemykin Prof Dr Viktor V Zhdankin |
| Institution: | 1. Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812 (USA);2. Department of Chemistry, College of St. Benedict/St. John's University, St. Joseph, MN 56374 (USA);3. Tomsk Polytechnic University, 634050 Tomsk (Russian Federation) |
| 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. |
| Keywords: | cyclopropanation reactions hypoiodous acid iodine oxidation small ring systems |