Stereochemical characterization of fluorinated 2-(phenanthren-1-yl)propionic acids by enantioselective high performance liquid chromatography analysis and electronic circular dichroism detection

Bertucci, Carlo; Pistolozzi, Marco; Tedesco, Daniele; Zanasi, Riccardo; Ruzziconi, Renzo; Pietra, Anna Maria Di

doi:10.1016/j.chroma.2011.10.090

Search citation statements

Order By: Relevance

Paper Sections

Select...

Quantum Mechanical Calculations1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2012

2023

Publication Types

Select...

Article3

Book1

Relationship

Self Cite2

Independent2

Authors

Journals

Cited by 4 publications

(1 citation statement)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The widespread interest for QM calculations of chiroptical properties has also been the subject of recent reviews dealing with HPLC-CD methods [44,45], and a schematic representation of stereochemical analysis by HPLC-CD and QM calculations is given in Fig. 6, based on the AC assessment of a fluorinated propionic acid derivative (3) [150].…”

Section: Quantum Mechanical Calculationsmentioning

confidence: 99%

Advantages of electronic circular dichroism detection for the stereochemical analysis and characterization of drugs and natural products by liquid chromatography

Bertucci¹,

Tedesco²

2012

Journal of Chromatography A

Self Cite

View full text Add to dashboard Cite

Section: Quantum Mechanical Calculationsmentioning

confidence: 99%

Advantages of electronic circular dichroism detection for the stereochemical analysis and characterization of drugs and natural products by liquid chromatography

Bertucci¹,

Tedesco²

2012

Journal of Chromatography A

Self Cite

View full text Add to dashboard Cite

High-Performance Liquid Chromatography Enantioseparations Using Macrocyclic Glycopeptide-Based Chiral Stationary Phases: An Overview

Ilisz

Orosz

Péter

2019

Methods in Molecular Biology

View full text Add to dashboard Cite

Cationic half-sandwich quinolinophaneoxazoline-based (η⁶-p-cymene)ruthenium(ii) complexes exhibiting different chirality types: synthesis and structural determination by complementary spectroscopic methods

et al. 2014

Self Cite

View full text Add to dashboard Cite

Novel, optically pure 2-{4-methyl[2]paracyclo[2](5,8)quinolinophan-2-yl}-4-aryl/alkyloxazolines (QUIPHANOX) exhibiting both planar and central chirality have been prepared by reacting (Rp)- and (Sp)-2-cyano-4-methyl[2]paracyclo[2](5,8)quinolinophane with 2-aryl/alkyl-2-aminoethanols. The reaction of each of the above N,N-ligands with [Ru(η(6)-p-cymene)Cl2]2 in methanol, in the presence of either NH4PF6 or NaBPh4, gave the corresponding half-sandwich [(η(6)-p-cymene)Ru(QUIPHANOX)Cl](+)Y(-), (Y(-) = PF6(-), BPh4(-)) as stable complex salts exhibiting planar and carbon- and metal-centered chirality. The unknown absolute configuration (AC) at the metal was determined by (1)H NMR and by theoretical calculations of electronic circular dichroism (ECD) spectra and subsequently confirmed by crystallographic X-ray analysis. (Rp) and (Sp)-ligands afforded (RRu)- and (SRu)-configured complexes, respectively, independent of the AC at the chiral carbon of the oxazoline moiety.

show abstract

Stereochemical characterization of fluorinated 2-(phenanthren-1-yl)propionic acids by enantioselective high performance liquid chromatography analysis and electronic circular dichroism detection

Cited by 4 publications

References 19 publications

Advantages of electronic circular dichroism detection for the stereochemical analysis and characterization of drugs and natural products by liquid chromatography

Advantages of electronic circular dichroism detection for the stereochemical analysis and characterization of drugs and natural products by liquid chromatography

High-Performance Liquid Chromatography Enantioseparations Using Macrocyclic Glycopeptide-Based Chiral Stationary Phases: An Overview

Cationic half-sandwich quinolinophaneoxazoline-based (η⁶-p-cymene)ruthenium(ii) complexes exhibiting different chirality types: synthesis and structural determination by complementary spectroscopic methods

Contact Info

Product

Resources

About

Stereochemical characterization of fluorinated 2-(phenanthren-1-yl)propionic acids by enantioselective high performance liquid chromatography analysis and electronic circular dichroism detection

Cited by 4 publications

References 19 publications

Advantages of electronic circular dichroism detection for the stereochemical analysis and characterization of drugs and natural products by liquid chromatography

Advantages of electronic circular dichroism detection for the stereochemical analysis and characterization of drugs and natural products by liquid chromatography

High-Performance Liquid Chromatography Enantioseparations Using Macrocyclic Glycopeptide-Based Chiral Stationary Phases: An Overview

Cationic half-sandwich quinolinophaneoxazoline-based (η6-p-cymene)ruthenium(ii) complexes exhibiting different chirality types: synthesis and structural determination by complementary spectroscopic methods

Contact Info

Product

Resources

About

Cationic half-sandwich quinolinophaneoxazoline-based (η⁶-p-cymene)ruthenium(ii) complexes exhibiting different chirality types: synthesis and structural determination by complementary spectroscopic methods