AI Article Synopsis
- Cyclic amines like pyrrolidine can react with 2-formylaryl malonates through a redox-annulation process that allows for both oxidation and reduction.
- This method is redox-neutral as it combines oxidative amine α-CH bond functionalization with reductive N-alkylation.
- The process enables the synthesis of important compounds, including (±)-thalictricavine and its epimer, and has led to the discovery of a mild amine-promoted dealkoxycarbonylation reaction.
Article Abstract
Cyclic amines such as pyrrolidine undergo redox-annulations with 2-formylaryl malonates. Concurrent oxidative amine α-CH bond functionalization and reductive N-alkylation render this transformation redox-neutral. This redox-Mannich process provides regioisomers of classic Reinhoudt reaction products as an entry to the tetrahydroprotoberberine core, enabling the synthesis of (±)-thalictricavine and its epimer. An unusually mild amine-promoted dealkoxycarbonylation was discovered in the course of these studies.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4808586 | PMC |
| http://dx.doi.org/10.1002/chem.201501667 | DOI Listing |
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