AI Article Synopsis
- Coumarins and 2-pyran derivatives are common in natural products, and merging them can lead to new bioactive compounds.
- This research focuses on a novel synthesis method using a chiral tertiary amine to catalyze a [4 + 2] cyclization reaction between 3-aroylcoumarines and benzyl 2,3-butadienoate.
- The process achieves high yields (up to 97%) and enantiomeric excess (90%) when using Kumar's specific chiral catalyst.
Article Abstract
Coumarins and 2-pyran derivatives are among the most commonly found structural units in natural products. Therefore, the introduction of 2-pyran moiety into the coumarin structural unit, i.e., dihydrocoumarin-fused dihydropyranones, is a potentially successful route for the identification of novel bioactive structures, and the synthesis of these structures has attracted continuing research interest. Herein, a chiral tertiary amine catalyzed [4 + 2] cyclization of 3-aroylcoumarines with benzyl 2,3-butadienoate was reported. In the presence of Kumar's 6'-(4-biphenyl)-β-iso-cinchonine, the desired dihydrocoumarin-fused dihydropyranone products could be obtained in up to 97% yield and 90% ee values.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7831925 | PMC |
| http://dx.doi.org/10.3390/molecules26020489 | DOI Listing |
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