(4R,5S)-1,5-DIMETHYL-4-PHENYLIMIDAZOLIDIN-2-ONE AS A CHIRAL AUXILIARYFOR THE DIASTEREOSELECTIVE ALKYLATION OF A NEW IMINIC GLYCINE DERIVATIVE - PRACTICAL ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS

Authors
GUILLENA G NAJERA C
Citation
G. Guillena et C. Najera, (4R,5S)-1,5-DIMETHYL-4-PHENYLIMIDAZOLIDIN-2-ONE AS A CHIRAL AUXILIARYFOR THE DIASTEREOSELECTIVE ALKYLATION OF A NEW IMINIC GLYCINE DERIVATIVE - PRACTICAL ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS, Tetrahedron : asymmetry, 9(7), 1998, pp. 1125-1129
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
7
Year of publication
1998
Pages
1125 - 1129
Database
ISI
SICI code
0957-4166(1998)9:7<1125:(AACA>2.0.ZU;2-P
Abstract
The lithium enolate of enantiomerically pure N-[bis(methylthio)methyle ne] glycinate 11 derived from (4R,5S)-1,5-dimethyl-4-phenylimidazolidi n-2-one reacts with alkyl halides giving the alkylated derivatives 12 with a high degree of control of the diastereoselectivity. These alkyl ated systems are easily hydrolyzed to the corresponding cx-amino acids , the chiral auxiliary being recovered. (C) 1998 Elsevier Science Ltd. All rights reserved.