title: Synthesis of enantiopure 1,4-dioxanes, morpholines, and piperazines from the reaction of chiral 1,2-diols, amino alcohols, and diamines with vinyl selenones.
abstract: The reactions of readily available vinyl selenones with enantiopure 1,2-diols, N-protected-1,2-aminoalcohols, and diamines gave substituted enantiopure 1,4-dioxanes, morpholines, and piperazines, respectively, in good to excellent yields. The same procedure was extended to the synthesis of thiomorpholine, benzodiazepine, and benzoxazepine. The reactions proceeded in one pot, in the presence of base, through a simple and novel application of the Michael-initiated, ring-closure (MIRC) reactions. The formed heterocycles constitute a framework that is observed in a large number of pharmaceutical compounds.
authors.affiliation: Dipartimento di Chimica e Tecnologia del Farmaco Sezione di Chimica Organica, Università di Perugia via del Liceo 1, Italy. bagnoli@unipg.it
authors.forename: Luana
authors.initials: L
authors.lastname: Bagnoli
authors.forename: Catalina
authors.initials: C
authors.lastname: Scarponi
authors.forename: Maria Giovanna
authors.initials: MG
authors.lastname: Rossi
authors.forename: Lorenzo
authors.initials: L
authors.lastname: Testaferri
authors.forename: Marcello
authors.initials: M
authors.lastname: Tiecco
mesh_terms: D000605:Amino Alcohols / Q000737:chemistry*; D003959:Diamines / Q000737:chemistry*; D004146:Dioxanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000605:Amino Alcohols; D003959:Diamines; D004146:Dioxanes; D009025:Morpholines; D010879:Piperazines; D014753:Vinyl Compounds; C025223:1,4-dioxane