D-glucose-based azacrown ethers with a phosphonoalkyl side chain: application as enantioselective phase transfer catalysts

Authors
Bako, P Novak, T Ludanyi, K Pete, B Toke, L Keglevich, G
Citation
P. Bako et al., D-glucose-based azacrown ethers with a phosphonoalkyl side chain: application as enantioselective phase transfer catalysts, TETRAHEDR-A, 10(12), 1999, pp. 2373-2380
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
12
Year of publication
1999
Pages
2373 - 2380
Database
ISI
SICI code
0957-4166(19990618)10:12<2373:DAEWAP>2.0.ZU;2-T
Abstract
Five chiral alpha-D-glucose-based monoaza-15-crown-5 ethers with a phosphon oalkyl side chain 5a-e have been synthesized. The substituent at the nitrog en atom has a major influence on the cation extraction ability of the azacr own. The new lariat ethers 5a-e show significant asymmetric induction as ph ase transfer catalysts in the Michael addition of 2-nitropropane to chalcon e. (C) 1999 Elsevier Science Ltd. All rights reserved.