SYNTHESIS OF POLYSUBSTITUTED PYRROLIZIDINES FROM PROLINE DERIVATIVES AND CONJUGATED NITROOLEFINS

Authors
FELLUGA F PITACCO G VISINTIN C VALENTIN E
Citation
F. Felluga et al., SYNTHESIS OF POLYSUBSTITUTED PYRROLIZIDINES FROM PROLINE DERIVATIVES AND CONJUGATED NITROOLEFINS, Helvetica Chimica Acta, 80(5), 1997, pp. 1457-1472
Citations number
32
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
80
Issue
5
Year of publication
1997
Pages
1457 - 1472
Database
ISI
SICI code
0018-019X(1997)80:5<1457:SOPPFP>2.0.ZU;2-Y
Abstract
The stereochemistry of 1,3-dipolar cycloaddition of azomethine ylides derived from aromatic aldehydes and L-proline alkyl eaters with severa l nitroolefins was investigated. Cyclic and acyclic nitroolefins add t o the anti form of the ylide in a highly diastereoselective but poorly regioselective manner to give pyrrolizidine derivatives. In a few cas es, the stereochemical results strongly support a stepwise mechanism.