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


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.

SUBMITTER: Herbert SA 

PROVIDER: S-EPMC4273304 | BioStudies | 2014-01-01T00:00:00Z

REPOSITORIES: biostudies

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