Abstract
Aims: The aim of this study is to investigate the p-toluene sulphonic acid (p-Ts.OH)-catalyzed reaction of racemic-azetidine-2,3-diones with enantiomerically pure cis and trans-4-hydroxy-L-proline in refluxing ethanol culminating in a synthesis of substituted novel 3-(pyrrol-1-yl)-azetidin-2-ones at the C-3 position. Methods: This work describes an alternative synthetic route enabling the tandem transformation of proline to pyrrole, followed by intramolecular chirality transfer to the β-lactams ring. Results: All four diastereomers of 3-(pyrrol-1-yl)-azetidin-2-ones could be achieved in good to excellent yield with high diastereoselectivity in a single-pot operation. Conclusion: This method can be applied to other activated carbonyl compounds and functionalized pyr-roles can be obtained through an expeditious process.
Original language | English |
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Pages (from-to) | 337-345 |
Number of pages | 9 |
Journal | Current Organocatalysis |
Volume | 9 |
Issue number | 4 |
DOIs | |
State | Published - Dec 2022 |
Externally published | Yes |
Keywords
- B-lactam
- L-proline
- Staudinger reaction
- anti-cancer
- hydroxyl prolines
- pyrrole