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Synthesis and Reactions of 2‐[1‐Methyl‐1‐(pyrrolidin‐2‐yl)ethyl]‐1 H ‐pyrrole and Some Derivatives with Aldehydes: Chiral Structures Combining a Secondary‐Amine Group with an 1 H ‐Pyrrole Moiety as Excellent H‐Bond Donor
Author(s) -
Pordea Anca,
StoeckliEvans Helen,
Dalvit Claudio,
Neier Reinhard
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200459
Subject(s) - chemistry , pyrrolidine , pyrrole , iminium , moiety , amine gas treating , ring (chemistry) , nucleophile , piperidine , medicinal chemistry , stereochemistry , organic chemistry , ion , catalysis
The synthesis of compound 2 and its derivatives 6 and 8 combining a pyrrolidine ring with an 1 H ‐pyrrole unit is described ( Scheme 2 ). Their attempted usability as organocatalysts was not successful. Reacting these simple pyrrolidine derivatives with cinnamaldehyde led to the tricyclic products 3b, 9b , and 10b first ( Scheme 1, Fig. 2 ). The final, major products were the pyrrolo‐indolizidine tricycles 3a, 9a , and 10a obtained via the iminium ion reacting intramolecularly with the nucleophilic β ‐position of the 1 H ‐pyrrole moiety ( cf. Scheme 1 ).