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Inherently chiral calix[4]arenes via oxazoline directed ortholithiation : synthesis and probe of chiral space

Herbert, Simon A. ; Van Laeren, Laura Jane ; Castell, Dominic C. ; Arnott, Gareth E. (2014-11-25)

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.

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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.

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