Synthesis of Biaryl Atropisomers Using Dynamic Resolution
Author Information
Author(s): Bracegirdle Ann, Clayden Jonathan, Lai Lai Wah
Primary Institution: School of Chemistry, University of Manchester
Hypothesis
Can biaryl aldehydes be resolved in a dynamic fashion using (−)-ephedrine or a proline-derived diamine?
Conclusion
Biaryl aldehydes can be effectively resolved through dynamic resolution, achieving selectivities of up to 5:1 under specific conditions.
Supporting Evidence
- Selectivity of the dynamic resolution depends significantly on reaction conditions.
- Up to 5:1 selectivity was achieved with specific biaryl aldehydes.
- Water presence in the reaction mixture aids in achieving thermodynamic equilibrium.
Takeaway
This study shows how to make special chemical compounds called biaryl atropisomers by mixing them with certain other chemicals in a way that helps them separate into different forms.
Methodology
The study involved heating biaryl aldehydes with (−)-ephedrine or a proline-derived diamine in toluene under controlled conditions to achieve dynamic resolution.
Limitations
The selectivity was limited to a maximum of 5:1 and varied with reaction conditions.
Digital Object Identifier (DOI)
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