PREPARATION OF OPTICALLY-ACTIVE BETA-CARBOXYASPARTIC ACID-DERIVATIVESVIA PD(0)-CATALYZED ASYMMETRIC SUBSTITUTION OF SCHIFF-BASE ACETATES

Authors
ODONNELL MJ ZHOU CY CHEN N
Citation
Mj. Odonnell et al., PREPARATION OF OPTICALLY-ACTIVE BETA-CARBOXYASPARTIC ACID-DERIVATIVESVIA PD(0)-CATALYZED ASYMMETRIC SUBSTITUTION OF SCHIFF-BASE ACETATES, Tetrahedron : asymmetry, 7(3), 1996, pp. 621-624
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
3
Year of publication
1996
Pages
621 - 624
Database
ISI
SICI code
0957-4166(1996)7:3<621:POOBA>2.0.ZU;2-J
Abstract
Optically active beta-carboxyaspartic acid derivative 6 (77% ee) was o btained in 48% total yield from the coupling of Schiff base acetate 3 with sodium dimethyl malonate in the presence of 5% Pd(OAc)(2)-(2S,4S) -BPPM followed by a single recrystallization. Phase-transfer catalyzed alkylation of malonates 6 affords beta-substituted ASA derivatives 7 in excellent yield without racemization at the alpha-carbon. (C) 1996 Elsevier Science Ltd