title: Efficient synthesis of α,β-unsaturated alkylimines performed with allyl cations and azides: application to the synthesis of an ant venom alkaloid.
abstract: An efficient synthesis of α,β-unsaturated alkylimines at low temperature using azides has been developed. Carbocations generated from allyl alcohols helped achieve a rapid conversion under mild conditions with azides to afford reactive α,β-unsaturated imines. Hydroxy or alkoxy groups are essential for these transformations, and utilizing readily accessible allyl alcohols gave a wide extension of substrates. The efficiency of this novel method is demonstrated in the total synthesis of an iminium ant venom alkaloid.
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Ikoma, Nara 6300192, Japan.
authors.forename: Kyohei
authors.initials: K
authors.lastname: Hayashi
authors.forename: Hiroki
authors.initials: H
authors.lastname: Tanimoto
authors.forename: Huan
authors.initials: H
authors.lastname: Zhang
authors.forename: Tsumoru
authors.initials: T
authors.lastname: Morimoto
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Nishiyama
authors.forename: Kiyomi
authors.initials: K
authors.lastname: Kakiuchi
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000862:Ant Venoms / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D003364:Costa Rica; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000862:Ant Venoms; D001386:Azides; D007097:Imines