title: Novel supramolecular palladium catalyst for the asymmetric reduction of imines in aqueous media.
abstract: A novel approach to the asymmetric reduction of dihydro-beta-carboline derivatives to the corresponding tetrahydro-beta-carbolines is described based on the supramolecular lyophilized complex formed from beta-cyclodextrin/imines as an enzyme mimetic and palladium hydride as the reducing agent. The methodology allowed us to develop a short and efficient preparation of (R)-harmicine and (R)-deplancheine alkaloids in high overall yields and ee of 89 and 90%, respectively.
authors: Laboratory of Asymmetric Synthesis, Chemistry Institute of Natural Resources, Universidad de Talca, Talca, PO Box 747, Talca, Chile.
authors: Wender A
authors: WA
authors: da Silva
authors: Manoel T
authors: MT
authors: Rodrigues
authors: N
authors: N
authors: Shankaraiah
authors: Renan B
authors: RB
authors: Ferreira
authors: Carlos Kleber Z
authors: CK
authors: Andrade
authors: Ronaldo A
authors: RA
authors: Pilli
authors: Leonardo S
authors: LS
authors: Santos
mesh_terms: D002243:Carbolines / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: D002243:Carbolines; D007097:Imines; D026121:Indole Alkaloids; C496494:deplancheine; C544842:harmicine; D014867:Water; C032391:palladium hydride; D010165:Palladium