title: Highly cis-selective synthesis of iodo-aziridines using diiodomethyllithium and in situ generated N-Boc-imines.
abstract: The first preparation of iodoaziridines is described. The addition of diiodomethyllithium to N-Boc-imines affords these novel aziridines in high yields. The reaction proceeds in one-pot via a highly diastereoselective cyclisation of an amino gem-diiodide intermediate.
authors.affiliation: Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK. j.bull@imperial.ac.uk
authors.forename: James A
authors.initials: JA
authors.lastname: Bull
authors.forename: Tom
authors.initials: T
authors.lastname: Boultwood
authors.forename: Thomas A
authors.initials: TA
authors.lastname: Taylor
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D018020:Lithium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013441:Sulfinic Acids / Q000737:chemistry
chemical_list: D001388:Aziridines; D007097:Imines; D018020:Lithium Compounds; D013441:Sulfinic Acids; C033132:aziridine; D007455:Iodine