title: Stereoselective synthesis of 3-substituted tetrahydropyrazinoisoquinolines via intramolecular cyclization of enantiomerically enriched dihydro-2H-pyrazines.
abstract: The preparation of 3-substituted tetrahydropyrazinoisoquinolines using the tributyltin hydride mediated intramolecular radical cyclization of suitably protected 2-substituted 3,4-dihydropyrazines is reported. The compounds are obtained as single enantiomers, as the relative configuration of the new generated stereogenic center is driven by the stereochemistry of the 2-substituted carbon in the starting materials, which is in turn derived from naturally occurring amino acids.
authors: ICCOM - CNR, Via Madonna del Piano 1, 50019 Sesto Fiorentino, Italy.
authors: Gianna
authors: G
authors: Reginato
authors: Maria Pia
authors: MP
authors: Catalani
authors: Bernardo
authors: B
authors: Pezzati
authors: Romano
authors: R
authors: Di Fabio
authors: Andrea
authors: A
authors: Bernardelli
authors: Ornella
authors: O
authors: Curcuruto
authors: Elisa
authors: E
authors: Moro
authors: Alfonso
authors: A
authors: Pozzan
authors: Alessandro
authors: A
authors: Mordini
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D006575:Heterocyclic Compounds, 3-Ring; D007546:Isoquinolines; D011719:Pyrazines