Inherently chiral calixarenes via oxazoline directed ortholithiation : synthesis and probe of chiral space
Please cite as follows: Herbert, S. A., Van Laeren, L. J., Castell, D. C. & Arnott, G. E. 2014. Inherently chiral calixarenes 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 diastereoselective oxazoline-directed lithiation of calixarenes 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 calixarenes 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.