Synthesis of new chiral macrocycles-based glycolipids and its application in asymmetric Michael addition
Document Type
Article
Publication Date
7-1-2021
Abstract
A series of new mix aza- and thia-macrocyclic glycolipids (9, 111, 16 and 17) have been synthesized and their enantiomeric selectivity was studied. The synthesis of the macrocycles involved a simple protection of two hydroxyl groups of the glycolipids followed by building up the mix-heteroatom macrocyclic in simple sequences. The macrocycles and previously investigated analogues (la, n, a and 21) have been applied as phase transfer catalysts in the enantioselective Michael addition of 2-nitropropane to chalcone and showed good-to-excellent enantiomer excess (ee). Among the catalysts, the galactose aza-crown ether-based glycolipid 21 proved to be the most effective with 90% ee.
Keywords
Chiral macrocycles-based glycolipids, Asymmetric Michael addition, New mix aza-
Divisions
CHEMISTRY
Funders
Science and Technology Development Fund (STDF), Ministry of Higher Education & Scientific Research (MHESR),Universiti Malaya (UM.C/625/1/HIR/MOHE/05)
Publication Title
Research on Chemical Intermediates
Volume
47
Issue
7
Publisher
Springer Verlag
Publisher Location
VAN GODEWIJCKSTRAAT 30, 3311 GZ DORDRECHT, NETHERLANDS