title: Alkylative ring opening of N-methylaziridinium ions and a formal synthesis of tyroscherin.
abstract: Alkylative ring-opening reactions of stable 2-substituted N-methylaziridinium ions proceeded with various alkyl- or arylmagnesium bromides in the presence of CuI to yield synthetically valuable and optically pure alkylated acyclic amines in a completely regio- and stereoselective manner. This was applied to a formal synthesis of the cytotoxic natural product tyroscherin.
authors.affiliation: Department of Chemistry and Protein Centre for Bio-Industry, Hankuk University of Foreign Studies, Yongin 449-791, Korea.
authors.forename: Doo-Ha
authors.initials: DH
authors.lastname: Yoon
authors.forename: Philjun
authors.initials: P
authors.lastname: Kang
authors.forename: Won Koo
authors.initials: WK
authors.lastname: Lee
authors.forename: Yongeun
authors.initials: Y
authors.lastname: Kim
authors.forename: Hyun-Joon
authors.initials: HJ
authors.lastname: Ha
mesh_terms: D000478:Alkylation; D001388:Aziridines / Q000737:chemistry*; D004837:Epinephrine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D005233:Fatty Alcohols / Q000138:chemical synthesis*; D007477:Ions / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure
chemical_list: D001388:Aziridines; D005233:Fatty Alcohols; D007477:Ions; C495800:tyroscherin; D004837:Epinephrine