Novel supramolecular palladium catalyst for the asymmetric reduction of imines in aqueous media.
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.
da Silva
Wender A
WA
Laboratory of Asymmetric Synthesis, Chemistry Institute of Natural Resources, Universidad de Talca, Talca, PO Box 747, Talca, Chile.
Rodrigues
Manoel T
MT
Shankaraiah
N
N
Ferreira
Renan B
RB
Andrade
Carlos Kleber Z
CK
Pilli
Ronaldo A
RA
Santos
Leonardo S
LS
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
D002243:Carbolines; D007097:Imines; D026121:Indole Alkaloids; C496494:deplancheine; C544842:harmicine; D014867:Water; C032391:palladium hydride; D010165:Palladium