Overcoming regioselectivity issues inherent in bis-Tröger's base preparation
Martin Havlík1, Vladimír Kral, Bohumil Dolenský
1Department of Analytical Chemistry, Institute of Chemical Technology, Prague, Technicka 5, 166 28 Praha 6, Czech Republic.
Organic Letters
|October 6, 2006
Summary
Researchers developed a new synthesis for bis-Tröger
Area of Science:
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Bis-Tröger's base (bis-TB) derivatives represent a novel class of molecular tweezers.
- A significant limitation in studying bis-TB derivatives is the scarcity of commercially available ortho-nitrocarboxylic acid precursors.
Purpose of the Study:
- To present a novel reverse synthetic strategy for accessing bis-Tröger's base derivatives.
- To overcome the precursor availability issue for bis-TB synthesis.
Main Methods:
- A reverse synthetic approach was employed, starting from readily available dinitrodicarboxylic acids.
- The methodology utilizes common and commercially available aromatic amines.
Main Results:
- Regioisomeric bis-Tröger's base derivatives were successfully prepared.
- The synthetic strategy circumvents the need for specialized ortho-nitrocarboxylic acid precursors.
Conclusions:
- The presented reverse synthetic strategy provides a viable route to bis-Tröger's base derivatives.
- This method facilitates the selective preparation of regioisomeric bis-TB compounds using accessible starting materials.
