Ginotra, Sandeep K. ; Singh, Vinod K. (2006) Studies on enantioselective allylic oxidation of olefins using peresters catalyzed by Cu(I)-complexes of chiral pybox ligands Organic and Biomolecular Chemistry, 4 (23). pp. 4370-4374. ISSN 1477-0520
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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/2006...
Related URL: http://dx.doi.org/10.1039/B612423B
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 π–π stacking model has been proposed and discussed to explain the stereochemical outcome of the reaction.
Item Type: | Article |
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Source: | Copyright of this article belongs to Royal Society of Chemistry. |
ID Code: | 55420 |
Deposited On: | 18 Aug 2011 08:42 |
Last Modified: | 18 May 2016 07:41 |
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