Monomeric and Dimeric 9-O Anthraquinone and Phenanthryl Derivatives of Cinchona Alkaloids as Chiral Solvating Agents for the NMR Enantiodiscrimination of Chiral Hemiesters

Chirality

Volumn 27, Issue 10, 2015, Pages 693-699

  Uccello Barretta, Gloria ^a   Mandoli, Alessandro ^a   Balzano, Federica ^a   Aiello, Federica ^a   De Nicola, Beatrice ^a   Del Grande, Alessandro ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

chiral solvating agents; cinchona alkaloids; enantiodiscrimination phenomena; hemiesters; NMR spectroscopy

Indexed keywords

ANTHRAQUINONE DERIVATIVE; CINCHONA ALKALOID; DIMER; MONOMER;

ARTICLE; CHIRAL CHROMATOGRAPHY; CHIRALITY; COMPLEX FORMATION; CONFORMATION; CONTROLLED STUDY; ENANTIOMER; HETERONUCLEAR SINGLE QUANTUM COHERENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY; SYNTHESIS; THERMODYNAMICS;

EID: 84942824461     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22488     Document Type: Article

References (16)

1. Jacques J, Collet A, Wilen SH,. Enantiomers, racemates and resolutions. New York: John Wiley and Sons; 1981.
2. Marcelli T, Hiemstra H,. Cinchona alkaloids in asymmetric organocatalysis. Synthesis 2010; 2010: 1229-1279.
3. Duan J, Li P,. Asymmetric organocatalysis mediated by primary amines derived from cinchona alkaloids: recent advances. Catal Sci Technol 2014; 4: 311-320.
4. Zheng S, Schienebeck CM, Zhang W, Wang HY, Tang W,. Cinchona alkaloids as organocatalysts in enantioselective halofunctionalization of alkenes and alkynes. Asian J Org Chem 2014; 3: 366-376.
5. Babu SA, Anand RV, Ramasastry SSV,. Cinchona alkaloid-catalyzed stereoselective carbon-carbon bond forming reactions. Recent Pat Catal 2013; 2: 47-67.
6. Boratyński P,. Dimeric Cinchona alkaloids. Mol Divers 2015; 19: 385-422.
7. Kacprzak K, Gawronski J,. Resolution of racemates and enantioselective analytics by cinchona alkaloids and their derivatives. In:, Song CE, editor, Cinchona alkaloids in synthesis and catalysis. Wiley-VCH: Weinheim, Germany; 2009. p 421-469.
8. Lammerhofer M, Lindner W,. Liquid chromatographic enantiomer separation and chiral recognition by cinchona alkaloid-derived enantioselective separation materials. Adv Chromatogr (Boca Raton, FL) 2008; 46: 1-107.
9. McCalley DV,. Analysis of the cinchona alkaloids by high-performance liquid chromatography and other separation techniques. J Chromatogr A 2002; 967: 1-19.
10. Uccello-Barretta G, Balzano F,. Chiral NMR solvating additives for differentiation of enantiomers. Top Curr Chem 2013; 341: 69-131.
11. Uccello Barretta G, Vanni L, Balzano F,. Nuclear magnetic resonance approaches to the rationalization of chromatographic enantiorecognition processes. J Chromatogr A 2010; 1217: 928-940.
12. Balzano F, Jumde RP, Mandoli A, Masi S, Pini D, Uccello Barretta G,. Mono- and bis-quinidine organicatalysis in the asymmetric methanolysis of cis-1,2,3,6-tetrahydrophtalic anhydride: a conformational and mechanistic NMR study. Chirality 2011; 23: 784-795.
13. Homer J, Perry MJ,. Molecular complexes. Part 18. A nuclear magnetic resonance adaptation of the continuous variation (Job) method of stoichiometry determination. Chem Soc Faraday Trans 1 1986; 82: 533-543.
14. Li H, Liu X, Wu F, Tang L, Deng L,. Elucidation of the active conformation of cinchona alkaloid catalyst and chemical mechanism of alcoholysis of meso anhydrides. Proc Natl Acad Sci U S A 2010; 107: 20625-20629.
15. Cheng SK, Zhang SY, Wang PA, Kuang YQ, Sun XL,. Homogeneous catalytic asymmetric dihydroxylation of olefins induced by an efficient and recoverable polymer-bound ligand QN-AQN-OPEG-OMe. Appl Organometal Chem 2005; 19: 975-979.
16. Burgi T, Baiker A,. Conformational behavior of cinchonidine in different solvents: a combined NMR and ab initio investigation. J Am Chem Soc 1998; 120: 12920-12926.