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Atroposelective Arene-Forming Alkene Metathesis.
Zlatko Jončev1,2, Christof Sparr1,2
1Department of Chemistry, University of Basel, Johanns-Ring 19, 4056, Basel, Switzerland.
Alkene metathesis now controls stereogenic axes through traceless arene formation. This breakthrough enables selective synthesis of complex molecules like binaphthalene atropisomers with high enantioselectivity.
Area of Science:
- Organic Chemistry
- Catalysis
- Stereoselective Synthesis
Background:
- Alkene metathesis with chiral catalysts creates defined stereocenters in aliphatic compounds.
- Controlling stereogenic units in aromatic structures via alkene metathesis remained a significant challenge.
Purpose of the Study:
- To explore alkene metathesis for catalytic control of stereogenic axes.
- To achieve traceless arene formation for stereoselective synthesis.
Main Methods:
- Utilized enantiopure metal alkylidene complexes for catalysis.
- Employed stereodynamic trienes as substrates.
- Applied a chiral molybdenum catalyst.
Main Results:
- Demonstrated selective conversion of trienes to binaphthalene atropisomers.
- Achieved high enantioselectivities up to 98:2 e.r. (enantiomeric ratio).
- Obtained excellent product yields.
Conclusions:
- Stereoselective, arene-forming metathesis is feasible for controlling stereogenic axes.
- This method offers versatile routes to complex molecular architectures with defined configurations.
- Anticipated to enable synthesis of diverse molecular topologies.
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