Synthesis of new chiral macrocycles-based glycolipids and its application in asymmetric Michael addition
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 macro...
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| Main Authors: | , , |
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| Format: | Article |
| Published: |
Springer Verlag
2021
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| Subjects: | |
| Online Access: | http://eprints.um.edu.my/26974/ |
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| Institution: | Universiti Malaya |
| Summary: | 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. |
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