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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Efficient base catalyzed alkylation reactions with aziridine electrophiles
Thomas A Moss1, Aurelie Alba, David Hepworth
1School of Chemistry, The University of Manchester, Oxford Road, Manchester, UKM13 9PL.
Chemical Communications (Cambridge, England)
|May 21, 2008
Summary
N-Mesitylene sulfonyl and N-tosyl aziridines are effective electrophiles for alkylation reactions. The organic phosphorine base BEMP efficiently catalyzes these reactions, achieving high yields under mild conditions.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Aziridines are strained three-membered heterocycles.
- Electrophilic aziridines are valuable synthetic intermediates.
- Carbon acid alkylation is a fundamental transformation in organic synthesis.
Purpose of the Study:
- To identify effective electrophiles for the alkylation of carbon acids.
- To investigate the catalytic activity of the organic phosphorine base BEMP.
- To develop mild and efficient reaction conditions for C-C bond formation.
Main Methods:
- Utilized N-mesitylene sulfonyl and N-tosyl aziridines as electrophiles.
- Employed the organic phosphorine base BEMP as a catalyst.
- Performed alkylation reactions with various pro-nucleophiles.
Main Results:
- N-Mesitylene sulfonyl and N-tosyl aziridines demonstrated high reactivity as electrophiles.
- BEMP effectively catalyzed the alkylation of carbon acids.
- Yields up to 99% were achieved for a range of pro-nucleophiles.
- The reactions proceeded under mild conditions.
Conclusions:
- N-Mesitylene sulfonyl and N-tosyl aziridines are potent electrophiles for carbon acid alkylation.
- BEMP is a highly effective catalyst for this transformation.
- The developed method offers a mild and efficient route to alkylated products.
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