title: Monomeric and dimeric 9-O anthraquinone and phenanthryl derivatives of cinchona alkaloids as chiral solvating agents for the NMR enantiodiscrimination of chiral hemiesters.
abstract: Mono- and bis-alkaloid chiral auxiliaries with anthraquinone or phenanthryl cores were probed as chiral solvating agents (CSAs) for the enantiodiscrimination of chiral cyclic hemiesters. The dimeric anthraquinone derivative and the monomeric phenanthryl one showed remarkable efficiency in the nuclear magnetic resonance (NMR) differentiation of enantiomeric mixtures of hemiesters. An anthraquinone analogous with a single alkaloid unit was remarkably less effective. The conformational prevalence of the chiral auxiliaries were ascertained by NMR.
authors.affiliation: Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Pisa, Italy.
authors.forename: Gloria
authors.initials: G
authors.lastname: Uccello Barretta
authors.affiliation: Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Pisa, Italy.
authors.forename: Alessandro
authors.initials: A
authors.lastname: Mandoli
authors.affiliation: Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Pisa, Italy.
authors.forename: Federica
authors.initials: F
authors.lastname: Balzano
authors.affiliation: Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Pisa, Italy.
authors.forename: Federica
authors.initials: F
authors.lastname: Aiello
authors.affiliation: Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Pisa, Italy.
authors.forename: Beatrice
authors.initials: B
authors.lastname: De Nicola
authors.affiliation: Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Pisa, Italy.
authors.forename: Alessandro
authors.initials: A
authors.lastname: Del Grande
keywords: NMR spectroscopy; chiral solvating agents; cinchona alkaloids; enantiodiscrimination phenomena; hemiesters