Jump to main content
Jump to site search

Issue 11, 2011
Previous Article Next Article

C-hexaphenyl-substituted trianglamine as a chiral solvating agent for carboxylic acids

Author affiliations

Abstract

Chiral hexaazamacrocycles with a trianglamine structure and C3-symmetry, containing six ring substituents and twelve stereocenters have been tested as chiral solvating agents (CSAs) for α-substituted carboxylic acids. Excellent results have been obtained with a hexaphenyl-substituted macrocycle. The optimal ratio between the macrocycle and racemic acid, allowing for baseline separation of the enantiomers’ signals in the 1H NMR spectrum, was dependent on the type of acid, in particular on its degree of acidity. The analyte and the CSA could be separated and recovered by a simple acid–base extraction and reused without purification. The conformations of the free and protonated hexaamino macrocycles were inferred by CD spectroscopic studies and DFT calculations.

Graphical abstract: C-hexaphenyl-substituted trianglamine as a chiral solvating agent for carboxylic acids

Back to tab navigation

Supplementary files

Publication details

The article was received on 16 Dec 2010, accepted on 17 Mar 2011 and first published on 18 Apr 2011


Article type: Paper
DOI: 10.1039/C0OB01192D
Citation: Org. Biomol. Chem., 2011,9, 4234-4241
  •   Request permissions

    C-hexaphenyl-substituted trianglamine as a chiral solvating agent for carboxylic acids

    A. Gualandi, S. Grilli, D. Savoia, M. Kwit and J. Gawroński, Org. Biomol. Chem., 2011, 9, 4234
    DOI: 10.1039/C0OB01192D

Search articles by author

Spotlight

Advertisements