Modification of diphenylamine-linked bis(oxazoline) ligands: Tuning of electronic effect and rigidity of ligand skeleton |
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Authors: | Han Liu Wei Li DaMing Du |
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Institution: | (1) Department of Chemistry, University of Vermont, 82 University Place, Burlington, VT 05405, USA; |
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Abstract: | The electronic effect of diphenylamine-linked bis(oxazoline) ligands was tuned through introduction of electron-withdrawing
bromo and nitro substituents onto the 4 and 4′ position. The variation of the NH bond acidity was determined by the different
chemical shifts of NH. The catalytic activity and enantioselectivity of the modified ligands were tested in the asymmetric
Friedel-Crafts alkylation of indole with β-nitrostyrene. The effect of ligand skeleton rigidity was also investigated through
the synthesis of iminodibenzyl-linked bis(oxazoline) ligands and evaluation of their catalytic activity in Friedel-Crafts
alkylation. |
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Keywords: | |
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