Jump to main content
Jump to site search

Issue 8, 2010
Previous Article Next Article

Synthesis of a chiral artificial receptor with catalytic activity in Michael additions and its chiral resolution by a new methodology

Author affiliations

Abstract

Xanthone derivatives were tested as organocatalysts for the Michael addition of pyrrolidine to an α,β-unsaturated lactam. The receptors combine a double H-bond donor pattern that resembles the oxyanion hole in natural enzymes, with a sulfone or sulfoxide that acts as a proton-transfer group. Since these compounds cannot be obtained enantiomerically pure from natural sources, chiral resolution was necessary to study their enantioselectivity. For the most promising receptor, this was accomplished using a new methodology that exploits its supramolecular interactions with a chiral guest and that is inspired in dynamic combinatorial chemistry. The success in the resolution of the racemic mixture indicates that this new method offers an alternative to kinetic resolution.

Graphical abstract: Synthesis of a chiral artificial receptor with catalytic activity in Michael additions and its chiral resolution by a new methodology

Back to tab navigation

Supplementary files

Publication details

The article was received on 02 Dec 2009, accepted on 25 Feb 2010 and first published on 08 Mar 2010


Article type: Communication
DOI: 10.1039/B925367J
Org. Biomol. Chem., 2010,8, 1763-1768

  •   Request permissions

    Synthesis of a chiral artificial receptor with catalytic activity in Michael additions and its chiral resolution by a new methodology

    L. Simón, F. M. Muñiz, Á. F. de Arriba, V. Alcázar, C. Raposo and J. R. Morán, Org. Biomol. Chem., 2010, 8, 1763
    DOI: 10.1039/B925367J

Search articles by author

Spotlight

Advertisements