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Title: Synthesis, extraction ability and application in asymmetric synthesis of azacrown ethers derived from D-glucose
Authors: Bako, P ×
Vizvardi, Kristof
Toppet, Suzanne
Van der Eycken, Erik
Hoornaert, GJ
Toke, L #
Issue Date: Jan-1998
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:54 issue:49 pages:14975-14988
Abstract: A number of new chiral monoaza-15-crown-5 derivatives (4-9) and lariat ethers (10-15) anellated to phenyl-beta-D-glucopyranoside have been synthesized. Their extracting ability was measured with alkali metal (Li, Na, K) and ammonium cations. The derivatives show significant asymmetric induction as phase transfer catalysts in the Michael addition of 2-nitropropane to chalcone (82% ee) although in low yield, and in the Darzens condensation of phenacyl chloride with benzaldehyde (74% ee). The substituent at the nitrogen atom of the crown ethers has a major influence on both the extraction ability and the enantioselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
Faculty of Science - miscellaneous
× corresponding author
# (joint) last author

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