Enantioselective solution- and solid-phase synthesis of glutamic acid derivatives via Michael addition reactions

Authors
O'Donnell, MJ Delgado, F Dominguez, E de Blas, J Scott, WL
Citation
Mj. O'Donnell et al., Enantioselective solution- and solid-phase synthesis of glutamic acid derivatives via Michael addition reactions, TETRAHEDR-A, 12(6), 2001, pp. 821-828
Citations number
108
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
6
Year of publication
2001
Pages
821 - 828
Database
ISI
SICI code
0957-4166(20010417)12:6<821:ESASSO>2.0.ZU;2-P
Abstract
The enantioselective conjugate addition of Schiff base ester derivatives to Michael accepters either in solution (56-89% e.e.) or on solid-phase (34-8 2% e.e.) gave optically active unnatural alpha -amino acid derivatives. The reaction was conducted in the presence of chiral, non-racemic quaternary s alts derived from the cinchona alkaloids using neutral, non-ionic phosphaze ne bases. (C) 2001 Elsevier Science Ltd. All rights reserved.