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Synthesis of new chiral macrocycles-based glycolipids and its application in asymmetric Michael addition

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Abstract

A series of new mix aza- and thia-macrocyclic glycolipids (9, 10, 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 (18, 19, 20 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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Acknowledgment

The grant from Ministry of Higher Education and the University of Malaya for the High Impact Research Grant (UM.C/625/1/HIR/MOHE/05) is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Kufa, Najaf, 54001, Iraq

    Karem J. Sabah

  2. Centre for Fundamental and Frontier Sciences in Nanostructure Self-Assembly, Department of Chemistry, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia

    N. Idayu Zahid & Rauzah Hashim

Authors
  1. Karem J. Sabah
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  2. N. Idayu Zahid
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  3. Rauzah Hashim
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Correspondence to Karem J. Sabah.

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Sabah, K.J., Zahid, N.I. & Hashim, R. Synthesis of new chiral macrocycles-based glycolipids and its application in asymmetric Michael addition. Res Chem Intermed 47, 2653–2667 (2021). https://doi.org/10.1007/s11164-021-04432-8

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