title: Pd(0)-catalyzed tandem deprotection/cyclization of tetrahydro-β-carbolines on allenes: application to the synthesis of indolo[2,3-a]quinolizidines.
abstract: The pallado-catalyzed tandem deprotection/cyclization reaction of enantioenriched N-allyl tetrahydro-β-carbolines on allenes is described. The first step generates in situ a deprotected tetrahydro-β-carboline, which then undergoes a cyclization on the allene function via an intermediate π-allyl Pd(II) derivative. This reaction results in the synthesis of various chiral indolic tetracycles (mainly indolo[2,3a]quinolizidine derivatives) presenting a vinyl function.
authors.affiliation: Centre de Recherche de Gif , Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: Valerian
authors.initials: V
authors.lastname: Gobé
authors.forename: Xavier
authors.initials: X
authors.lastname: Guinchard
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D002243:Carbolines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D054837:Quinolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D002243:Carbolines; D006576:Heterocyclic Compounds, 4 or More Rings; D007211:Indoles; D054837:Quinolizidines; C025947:propadiene; D010165:Palladium