Accessing Chiral Pyrrolodiketopiperazines under Organocatalytic Conditions
Eider Duñabeitia1, Aitor Landa1, Rosa López1
1Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country (UPV-EHU), Manuel de Lardizabal 3, 20018 San Sebastián, Spain.
Organic Letters
|December 29, 2022
Summary
Chiral pyrrolodiketopiperazines are synthesized using organocatalysis. Bicyclic acylpyrrol lactims act as pronucleophiles in carbon-carbon bond formation, creating diverse heterocyclic scaffolds via Michael addition.
Area of Science:
- Organic Chemistry
- Asymmetric Synthesis
- Catalysis
Background:
- Pyrrolodiketopiperazines are important heterocyclic scaffolds.
- Organocatalysis offers a sustainable approach to complex molecule synthesis.
- Developing novel pronucleophiles is key for C-C bond formation.
Purpose of the Study:
- To demonstrate the utility of bicyclic acylpyrrol lactims as pronucleophiles.
- To achieve organocatalytic synthesis of chiral pyrrolodiketopiperazines.
- To explore the scope of Michael addition reactions with these scaffolds.
Main Methods:
- Utilized bicyclic acylpyrrol lactims as pronucleophiles.
- Employed ureidoaminal-derived Brønsted bases as organocatalysts.
- Performed Michael addition reactions with nitroolefins.
Main Results:
- Successfully synthesized chiral pyrrolodiketopiperazines.
- Demonstrated the pronucleophilic capacity of acylpyrrol lactims.
- Achieved high skeleton diversity in the resulting heterocyclic scaffolds.
Conclusions:
- Bicyclic acylpyrrol lactims are effective pronucleophiles in organocatalytic C-C bond formation.
- Ureidoaminal-derived Brønsted bases facilitate efficient Michael additions.
- This methodology provides access to diverse chiral pyrrolodiketopiperazine structures.
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