Inherently chiral calix[4]arenes via oxazoline directed ortholithiation : synthesis and probe of chiral space
Date
2014-11-25
Authors
Herbert, Simon A.
Van Laeren, Laura Jane
Castell, Dominic C.
Arnott, Gareth E.
Journal Title
Journal ISSN
Volume Title
Publisher
Beilstein-Institut
Abstract
The diastereoselective oxazoline-directed lithiation of calix[4]arenes is reported with diastereoselective ratios of greater than 100:1 in some instances. Notably, it has been found that the opposite diastereomer can be accessed via this approach merely through the choice of an alkyllithium reagent. The inherently chiral oxazoline calix[4]arenes have also been preliminarily examined as ligands in the palladium-catalyzed Tsuji–Trost allylation reaction, returning results comparable to their planar chiral ferrocene counterparts pointing towards future application of these types of compounds.
Description
Please cite as follows: Herbert, S. A., Van Laeren, L. J., Castell, D. C. & Arnott, G. E. 2014. Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space. Beilstein Journal of Organic Chemistry, 10:2751–2755, doi:10.3762/bjoc.10.291.
The original publication is available at http://www.beilstein-journals.org/bjoc
The original publication is available at http://www.beilstein-journals.org/bjoc
Keywords
Calixarenes, Ortholithiation, Oxazoline, Tsuji–Trost, Supramolecular chemistry
Citation
Herbert, S. A., Van Laeren, L. J., Castell, D. C. & Arnott, G. E. 2014. Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space. Beilstein Journal of Organic Chemistry, 10:2751–2755, doi:10.3762/bjoc.10.291.