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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
A Nanovessel-Catalyzed Three-Component Aza-Darzens Reaction
Stephen M Bierschenk1, Robert G Bergman1, Kenneth N Raymond1
1Chemical Sciences Division, Lawrence Berkeley National Laboratory and Department of Chemistry , University of California , Berkeley , California 94720 , United States.
Supramolecular host catalysis enables a three-component Aza-Darzens reaction, yielding N-phenylaziridines. This supramolecular approach achieves stereoselectivity opposite to bulk solution, advancing complex organic synthesis.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Catalysis
Background:
- Nanovessels demonstrate catalytic competence in organic transformations.
- Supramolecular assemblies require catalysis of complex reactions to be standard reagents.
Purpose of the Study:
- To report a three-component Aza-Darzens reaction catalyzed by a supramolecular host.
- To generate N-phenylaziridines with specific stereochemistry.
Main Methods:
- Utilized a supramolecular host to catalyze a three-component Aza-Darzens reaction.
- Investigated the stereochemical outcome of the reaction in bulk solution versus supramolecular assembly.
Main Results:
- Achieved a three-component coupling within a supramolecular assembly.
- Generated N-phenylaziridines with the trans stereoisomer, opposite to the cis isomer formed in bulk solution.
Conclusions:
- Supramolecular host catalysis offers a novel solution for challenging synthetic transformations.
- This study advances the use of supramolecular assemblies as catalysts in organic synthesis.
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