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.
authors.affiliation: Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812 (USA). vzhdanki@d.umn.edu.
authors.forename: Akira
authors.initials: A
authors.lastname: Yoshimura
authors.forename: Steven R
authors.initials: SR
authors.lastname: Koski
authors.forename: Brent J
authors.initials: BJ
authors.lastname: Kastern
authors.forename: Jonathan M
authors.initials: JM
authors.lastname: Fuchs
authors.forename: T Nicholas
authors.initials: TN
authors.lastname: Jones
authors.forename: Roza Y
authors.initials: RY
authors.lastname: Yusubova
authors.forename: Victor N
authors.initials: VN
authors.lastname: Nemykin
authors.forename: Viktor V
authors.initials: VV
authors.lastname: Zhdankin
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry; D017613:Iodine Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000475:Alkenes; D019380:Anti-HIV Agents; D003521:Cyclopropanes; D017613:Iodine Compounds; D018894:Reverse Transcriptase Inhibitors; C081961:hypoiodous acid; D007455:Iodine
keywords: cyclopropanation reactions; hypoiodous acid; iodine; oxidation; small ring systems