DIASTEREOSELECTIVE SYNTHESIS OF ALPHA-ALPHA-DISUBSTITUTED GAMMA-CARBOXYPYROGLUTAMATES VIA SM(III)-AZOMETHINE YLIDE CYCLOADDITIONS

Authors
ALVAREZIBARRA C CSAKY AG DESILANES IL QUIROGA ML
Citation
C. Alvarezibarra et al., DIASTEREOSELECTIVE SYNTHESIS OF ALPHA-ALPHA-DISUBSTITUTED GAMMA-CARBOXYPYROGLUTAMATES VIA SM(III)-AZOMETHINE YLIDE CYCLOADDITIONS, Journal of organic chemistry, 62(3), 1997, pp. 479-484
Citations number
63
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
3
Year of publication
1997
Pages
479 - 484
Database
ISI
SICI code
0022-3263(1997)62:3<479:DSOAG>2.0.ZU;2-F
Abstract
Sm(III)-azomethine ylides 2 have been generated from ketones 1. Cycloa ddition of ylides 2 with alpha,beta-unsaturated esters 3 through a tra nsition state chelation-controlled by the metal allowed for the asymme tric synthesis of gamma-carboxypyroglutamates having a quaternary alph a-carbon that are potentially useful in the synthesis of neuroprotecti ve agents.