5(4H)-OXAZOLONES .8. AN EFFICIENT SYNTHESIS OF DELTA(1)-PYRROLINE-2-CARBOXYLIC ACID-DERIVATIVES THROUGH MICHAEL AND WITTIG CONDENSATION

Authors
CLERICI F GELMI ML POCAR D RONDENA R
Citation
F. Clerici et al., 5(4H)-OXAZOLONES .8. AN EFFICIENT SYNTHESIS OF DELTA(1)-PYRROLINE-2-CARBOXYLIC ACID-DERIVATIVES THROUGH MICHAEL AND WITTIG CONDENSATION, Tetrahedron, 51(36), 1995, pp. 9985-9994
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
36
Year of publication
1995
Pages
9985 - 9994
Database
ISI
SICI code
0040-4020(1995)51:36<9985:5.AESO>2.0.ZU;2-T
Abstract
Reaction of oxazolones 4 with triphenylvinylphosphonium bromide 3 affo rded, through a Michael addition, the alpha-aminoesters 7 or acids 8 f unctionalized with a triphenylphosphonium group. Compounds 7 and 8 wer e transformed in good yields in the corresponding Delta(1)-pyrroline-2 -carboxylic acids 2 or esters 1 by intramolecular Wittig condensation in presence of sodium alkoxide in refluxing toluene. Intermolecular Wi ttig reaction of 7 with 4-nitrobenzalhdeyde afforded protected unsatur ated alpha-aminoesters 9.