title: [Asymmetric syntheses of azacycloalkanes by one-pot [1+2+n] cyclization].
abstract: Enantio- and diastereoselective one-pot synthesis of three- to seven-membered cis-azaheterocycles was achieved using a triggered asymmetric conjugate addition reaction of lithium amide with an enoate, followed by C- and N-alkylation of the resulting lithium 3-aminoenolate with α, ω-dihaloalkane, which can be regarded as a [1+2+n] cyclization. The usefulness of the developed methodology was clearly demonstrated by the short-step asymmetric syntheses of azirinomycin ester, nemonapride, and kopsinine.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Japan. Sharada@chiba-u.jp
authors.forename: Shingo
authors.initials: S
authors.lastname: Harada
mesh_terms: D001372:Aza Compounds / Q000138:chemical synthesis*; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*
chemical_list: D001372:Aza Compounds; D006571:Heterocyclic Compounds