ORGN 680 |
| We describe an approach to the assembly of mechanically interlocked rotaxane systems using a thermodynamically–controlled carbonyl condensation reaction. Under benign solution chemical conditions, this well-known chemistry converts aldehydes to bulky α,β–unsaturated diketone derivatives. In this manner we can obtain in high yield and in high purity model systems that demonstrate the formation of stoppered threads. Reversibility in stopper formation is demonstrated in a base catalyzed exchange experiment. Extension of this successful model chemistry involves the preparation of elongated aromatic dialdehydes that are suitable candidates for the formation of stable CD inclusion complexes, precursors to the desired rotaxanes. Simple modification of reaction conditions renders the thread formation chemistry irreversible, through an additional dehydration process, providing a means for “locking–in” of supramolecular structure after the thermodynamic assembly process. |
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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
Division of Organic Chemistry |