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Evaluation of a chiral cubane-based Schiff base ligand in asymmetric catalysis reactions

Biegasiewicz, Kyle F; Ingalsbe, Michelle L; St. Denis, Jeffrey D; Gleason, James L; Ho, Junming; Coote, Michelle; Savage, G Paul; Priefer, Ronny

Description

Recently, a novel chiral cubane-based Schiff base ligand was reported to yield modest enantioselectivity in the Henry reaction. To further explore the utility of this ligand in other asymmetric organic transformations, we evaluated its stereoselectivity in cyclopropanation and Michael addition reactions. Although there was no increase in stereocontrol, upon computational evaluation using both M06L and B3LYP calculations, it was revealed that a pseudo six-membered ring exists, through H-bonding...[Show more]

CollectionsANU Research Publications
Date published: 2012-10-22
Type: Journal article
URI: http://hdl.handle.net/1885/100841
Source: Beilstein Journal of Organic Chemistry
DOI: 10.3762/bjoc.8.207

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