Evaluating Binol-Aldehyde as a Chiral Derivatizing Agent for Diamines

Authors:

Rohan Ravindranath, Soon Mog So and Jik Chin

Department of Chemistry, University of Toronto, 80, St. George str., Toronto, Ontario M5S 3H6, Canada; jchin@chem.utoronto.ca

We have synthesized and tested a new binol-aldehyde compound 1, against five diamine compounds. Using 1H NMR (400 MHz) spectroscopy, stable diasteriomeric imine complexes between 1 and five diamines were formed. Chemical shift nonequivalences (up to 0.058 ppm) were obtained for imines. Linear calibration plot was obtained for determining the enantiopurity of diamines.

binol

aldehyde

chiral derivatizing agent

diamine

1H NMR spectroscopy

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