AI Article Synopsis
- A new method was created for synthesizing two different types of chemical compounds, β-lactams and α-amino acid derivatives, using isothiourea (ITU) as a catalyst by changing the solvent used during the process.
- The reaction involves a stereospecific Mannich reaction that generates intermediates, which can lead to different products depending on whether DCM/CHCN or EtOH is used as the solvent.
- Detailed studies confirmed that both types of compounds originate from the same intermediate stage, and various transformations of these compounds were also explored for further chemical diversity.
Article Abstract
A protocol for the chemically divergent synthesis of β-lactams and α-amino acid derivatives with isothiourea (ITU) catalysis by switching solvents was developed. The stereospecific Mannich reaction occurring between imine and C(1)-ammonium enolate generated zwitterionic intermediates, which underwent intramolecular lactamization and afforded β-lactam derivatives when DCM and CHCN were used as solvents. However, when EtOH was used as the solvent, the intermediates underwent an intermolecular esterification reaction, and α-amino acid derivatives were produced. Detailed mechanistic experiments were conducted to prove that these two kinds of products came from the same intermediates. Furthermore, chemically diversified transformations of β-lactam and α-amino acid derivatives were achieved.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8826511 | PMC |
| http://dx.doi.org/10.1039/d1sc06127e | DOI Listing |
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