American Chemical Society
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Novel Supramolecular Palladium Catalyst for the Asymmetric Reduction of Imines in Aqueous Media

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journal contribution
posted on 2009-08-06, 00:00 authored by Wender A. da Silva, Manoel T. Rodrigues, N. Shankaraiah, Renan B. Ferreira, Carlos Kleber Z. Andrade, Ronaldo A. Pilli, Leonardo S. Santos
A novel approach to the asymmetric reduction of dihydro-β-carboline derivatives to the corresponding tetrahydro-β-carbolines is described based on the supramolecular lyophilized complex formed from β-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.