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

Autor: Simon A. Herbert, Laura J. van Laeren, Dominic C. Castell, Gareth E. Arnott
Jazyk: angličtina
Rok vydání: 2014
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 10, Iss 1, Pp 2751-2755 (2014)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.10.291
Popis: 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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