Studies on enantioselective allylic oxidation of olefins using peresters catalyzed by Cu(I)-complexes of chiral pybox ligands |
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Authors: | Ginotra Sandeep K Singh Vinod K |
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Institution: | Department of Chemistry Indian Institute of Technology, Kanpur, India- 208 016. |
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Abstract: | Enantioselective allylic oxidation of olefins with various peresters, using a catalytic amount of Cu(I)-pybox complex, can be tuned to achieve high asymmetric induction (up to 98% ee) by choosing a unique combination of a ligand and a perester at room temperature. The asymmetric induction in the reaction strongly depends on the nature of the substituents attached to the aryl ring of peresters. The presence of a gem-diphenyl group at C-5 and secondary or tertiary alkyl substituents at the chiral center (C-4) of the oxazoline rings is crucial for high enantioselectivity. A pi-pi stacking model has been proposed and discussed to explain the stereochemical outcome of the reaction. |
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