Asymmetric synthesis of alpha-amino acids using polymer-supported Cinchonaalkaloid-derived ammonium salts as chiral phase-transfer catalysts

Authors
Chinchilla, R Mazon, P Najera, C
Citation
R. Chinchilla et al., Asymmetric synthesis of alpha-amino acids using polymer-supported Cinchonaalkaloid-derived ammonium salts as chiral phase-transfer catalysts, TETRAHEDR-A, 11(16), 2000, pp. 3277-3281
Citations number
47
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
16
Year of publication
2000
Pages
3277 - 3281
Database
ISI
SICI code
0957-4166(20000825)11:16<3277:ASOAAU>2.0.ZU;2-R
Abstract
Cinchonidine and cinchonine have been N-alkylated with Merrifield resin and employed as chiral phase-transfer catalysts for the enantioselective alkyl ation of enolates from N-(diphenylmethylene)glycine esters with activated e lectrophiles (up to 90% ee). The use of the polymer-supported cinchonidine ammonium salt afforded the corresponding (S)-isomers, whereas the (R)-isome rs were obtained using related cinchonine-supported polymers. (C) 2000 Else vier Science Ltd. All rights reserved.