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Selective synthesis of the two diastereomers of 5‐oxo‐1 H ‐pyrrolizine‐3‐carboxylic acid
Author(s) -
Turner William W.
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230203
Subject(s) - chemistry , diastereomer , epimer , pyrrolidine , acetic acid , toluene , pyrrole , carboxylic acid , organic chemistry , medicinal chemistry
The rhodium catalysed reduction of a 2,5‐disubstitued pyrrole 5 occurred selectively with the cis addition of hydrogen. The resulting cis ‐pyrrolidine was either cyclized without epimerization in refluxing toluene to the pyrrolizine 7 or with epimerization in refluxing acetic acid to the pyrrolizine 9 .
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