title: 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.
authors.affiliation: Department of Chemistry and Polymer Science, Stellenbosch University, Private Bag X1, Matieland 7602, South Africa.
authors.forename: Simon A
authors.initials: SA
authors.lastname: Herbert
authors.affiliation: Department of Chemistry and Polymer Science, Stellenbosch University, Private Bag X1, Matieland 7602, South Africa.
authors.forename: Laura J
authors.initials: LJ
authors.lastname: van Laeren
authors.affiliation: Department of Chemistry and Polymer Science, Stellenbosch University, Private Bag X1, Matieland 7602, South Africa.
authors.forename: Dominic C
authors.initials: DC
authors.lastname: Castell
authors.affiliation: Department of Chemistry and Polymer Science, Stellenbosch University, Private Bag X1, Matieland 7602, South Africa.
authors.forename: Gareth E
authors.initials: GE
authors.lastname: Arnott
keywords: Tsuji–Trost; calix[4]arene; inherently chiral; ortholithiation; oxazoline