title: Efficient and highly selective synthesis of enantiopure cis- or trans-3,4-disubstituted 1,2,3,4-tetrahydroisoquinolines.
abstract: An efficient synthesis of enantiopure 3,4-disubstituted 1,2,3,4-tetrahydroisoquinolines, by treatment of readily available (2R,1'S)- or (2S,1'S)-2-(1-aminoalkyl)epoxides with H(3)PO(4).BF(3) complex, under mild reaction conditions, is reported. Both enantiopure diastereoisomers (3S,4S)- and (3S,4R)-3-alkyl-4-hydroxymethyl-1,2,3,4-tetrahydroisoquinolines were available starting from the suitable syn- or anti-aminoepoxide, respectively. A mechanism based on an intramolecular Friedel-Crafts-type reaction has been proposed to explain these results.
authors.affiliation: Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Spain. jmcg@uniovi.es
authors.forename: José M
authors.initials: JM
authors.lastname: Concellón
authors.forename: Paula
authors.initials: P
authors.lastname: Tuya
authors.forename: Virginia
authors.initials: V
authors.lastname: del Solar
authors.forename: Santiago
authors.initials: S
authors.lastname: García-Granda
authors.forename: M Rosario
authors.initials: MR
authors.lastname: Díaz
mesh_terms: D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004852:Epoxy Compounds; D044005:Tetrahydroisoquinolines