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Published on: February 7, 2019
Supramolecular-directed chiral induction in biaryl derivatives
J Etxebarria1, H Degenbeck, A-S Felten
1Institute of Chemical Research of Catalonia (ICIQ), 43007 Tarragona, Spain.
The Journal of Organic Chemistry
|October 20, 2009
Summary
Chiral building blocks enable the creation of diastereomerically enriched complexes through thermodynamic control. The direction of chirality transfer can be switched by altering substituents on the chiral block.
Area of Science:
- Organic Chemistry
- Stereochemistry
- Supramolecular Chemistry
Background:
- Dynamic covalent chemistry offers pathways to complex molecular architectures.
- Chirality transfer is crucial for asymmetric synthesis and molecular recognition.
- Biaryl compounds are prevalent in pharmaceuticals and materials science.
Purpose of the Study:
- To develop a thermodynamically controlled method for generating diastereomerically enriched complexes.
- To achieve chirality transfer from an enantiopure building block to a biaryl system.
- To investigate the influence of substituents on the stereochemical outcome.
Main Methods:
- Utilizing a thermodynamically controlled resolution process.
- Employing an enantiopure chiral auxiliary for induction.
- Synthesizing and analyzing dynamically racemic biaryl derivatives.
Main Results:
- Successfully generated diastereomerically enriched complexes.
- Demonstrated efficient chirality transfer from the building block to the biaryl.
- Showcased a switchable sense of stereochemical induction based on the chiral block's substituents.
Conclusions:
- Thermodynamic control provides a robust strategy for diastereoselective complex formation.
- The developed method allows for tunable stereochemical outcomes in biaryl systems.
- This approach offers potential for creating complex chiral molecules with tailored properties.
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