SYNTHESIS OF CHIRAL 4-ALKYL 4-HYDROXY CYCLOPENTENONES VIA A DIASTEREOSELECTIVE TANDEM AZA-COPE MANNICH CYCLIZATION REACTION FROM ALDEHYDOSUGAR/

Authors
KUHN C LEGOUADEC G SKALTSOUNIS AL FLORENT JC
Citation
C. Kuhn et al., SYNTHESIS OF CHIRAL 4-ALKYL 4-HYDROXY CYCLOPENTENONES VIA A DIASTEREOSELECTIVE TANDEM AZA-COPE MANNICH CYCLIZATION REACTION FROM ALDEHYDOSUGAR/, Tetrahedron letters, 36(18), 1995, pp. 3137-3140
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
18
Year of publication
1995
Pages
3137 - 3140
Database
ISI
SICI code
0040-4039(1995)36:18<3137:SOC44C>2.0.ZU;2-6
Abstract
A convenient construction of chiral 4-hydroxy 2-cyclopentenones from a lpha-alkoxy aldehyde 6 derived from sugar is reported. A mechanism is proposed involving imine-enamine equilibrium, then alkylation with 2-a lkoxypropenyl iodide followed by a tandem 3-aza-Cope/intramolecular Ma nnich reaction in a one-pot process.