Synthesis and reactivity of N-sugar-maleimides: an access to novel highly substituted enantiopure pyrazolines |
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| Authors: | Naoufel Ben Hamadi Moncef Msaddek |
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| Institution: | Laboratory of Synthesis Heterocyclic and Natural Substances, Department of Chemistry, Faculty of Sciences of Monastir, Boulevard of Environment, 5000 Monastir, Tunisia |
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| Abstract: | Two diastereomeric isoxazolines were synthesized in a stereoselective manner with 6.64–20.36% diastereoisomeric excess. The cycloaddition of N-sugar-maleimide in the presence of MgBr2 afforded isoxazolines with high diasterioselectivities (76–84% de). The 1,3-dipolar cycloaddition reaction was diastereospecific and enantiomerically pure (3R,4S,5S,6S,3aR,6aS)-pyrazolines were obtained from N-sugar-maleimides via 1,3-proton migration. |
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