ORGN 637 |
| The design of novel methodologies for a rapid and modular construction of combinatorial libraries relies on the identification of appropriate scaffolds. Successful scaffolds should be easily accessible, possess diverse substitution patterns and functionalities, and allow for a rapid conversion into structurally complex organic molecules. We envisioned that α-N-substituted amides would provide such scaffolds featuring four side chains, which could be cyclized via variety of methods to afford complex N-heterocycles. In this presentation, we describe a new protocol for a one-pot construction of highly substituted hexahydro-1H-isoindolones. The method relies on a tandem Cu-catalyzed three-component coupling providing amides I followed by an intramolecular Diels-Alder reaction to afford isoindolones II. Isoindolone cores with various substituents R1-R6 were prepared, and further diversified via Pd-catalyzed cross-coupling reactions. Application of the protocol to solution phase parallel synthesis of combinatorial libraries will also be described.
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Asymmetric Reactions, Combinatorial Chemistry, Molecular Recognition and Self-Assembly, Proteins, Peptides, Amino Acids and Enzyme Inhibitors
8:00 PM-10:00 PM, Wednesday, March 28, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Sci-Mix
Division of Organic Chemistry |
