AI Article Synopsis
- α-Aryl-substituted pyrrolidines, commonly found in natural alkaloids, can be synthesized efficiently in one step using quinone monoacetal and DABCO.
- The researchers identified optimal conditions to remove the aryl group from these compounds.
- Interestingly, when the reaction was performed without an aryl nucleophile, it produced octahydro-dipyrroloquinoline, resembling the structure of the natural product incargranine B, in high yield.
Article Abstract
α-Aryl-substituted pyrrolidine moiety is found in many natural alkaloids. Starting from pyrrolidine, we were able to synthesize α-aryl-substituted pyrrolidines in one step using quinone monoacetal as the oxidizing agent and DABCO as the base. We also discovered the reaction condition needed to efficiently remove the -aryl moiety from the α-arylated product. When the above reaction was carried out without the addition of an aryl nucleophile, the reaction of pyrrolidine and quinone monoacetal in 2,2,2-trifluoroethanol afforded octahydro-dipyrroloquinoline in high yield, which has the same skeleton as that of natural product incargranine B.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11017964 | PMC |
| http://dx.doi.org/10.1039/d4ra00983e | DOI Listing |
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