ENANTIOSELECTIVE SYNTHESIS OF L-ISOSERINE AND D-ISOSERINE VIA ASYMMETRIC HYDROGENATION OF METHYL N-PHTHALOYL-3-AMINO-2-OXOPROPANOATE

Authors
NOZAKI K SATO N TAKAYA H
Citation
K. Nozaki et al., ENANTIOSELECTIVE SYNTHESIS OF L-ISOSERINE AND D-ISOSERINE VIA ASYMMETRIC HYDROGENATION OF METHYL N-PHTHALOYL-3-AMINO-2-OXOPROPANOATE, Tetrahedron : asymmetry, 4(10), 1993, pp. 2179-2182
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
4
Issue
10
Year of publication
1993
Pages
2179 - 2182
Database
ISI
SICI code
0957-4166(1993)4:10<2179:ESOLAD>2.0.ZU;2-I
Abstract
L- and D-isoserine were synthesized enantioselectively via asymmetric hydrogenation of 3-amino-2-oxoester 5 catalyzed by [RuCl(binap)(benzen e)]Cl. Recrystallization and deprotection of (S)-6 (81% ee) afforded e nantiomerically pure L-isoserine. The enantioface selection by the cat alyst was opposite to that observed in asymmetric hydrogenation of oth er 2-oxoesters, such as methyl phenylglyoxylate and methyl 2-oxocycloh exylacetate.