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Synthesis and Reactions of 2-[1-Methyl-1-(pyrrolidin-2-yl)ethyl]-1H-pyrrole and Some Derivatives with Aldehydes: Chiral Structures Combining a Secondary-Amine Group with an 1H-Pyrrole Moiety as Excellent H-Bond Donor
Date de parution
2012
In
Helv. Chim. Acta
Vol.
11
No
95
De la page
2249
A la page
2264
Mots-clés
- Hydrogen bond (of 2-[1-methyl-1-(pyrrolidin-2-yl)ethyl]-1H-pyrrole and derivs.)
- Regiochemistry
- Stereochemistry (of reactions of 2-[1-methyl-1-(pyrrolidin-2-yl)ethyl]-1H-pyrrole and derivs. with (E)-cinnamaldehyde)
- methylpyrrolidinylethylpyrrole prepn reaction cinnamaldehyde
- pyrrolidinylethylpyrrole prepn reaction cinnamaldehyde
Résumé
The synthesis of compd. I (R = H) and its derivs. I (R = CF3, CO2Me) combining a pyrrolidine ring with an 1H-pyrrole unit is described. Their attempted usability as organocatalysts was not successful. Reacting these simple pyrrolidine derivs. with (E)-cinnamaldehyde led to tricyclic products. The final, major products were the pyrroloindolizidine tricycles, e.g. II, obtained via the iminium ion reacting intramolecularly with the nucleophilic ?-position of the 1H-pyrrole moiety. [on SciFinder(R)]
Identifiants
Type de publication
journal article
