Issue 11, 2020

Amplification of the chiroptical response of UV-transparent amines and alcohols by N-phthalimide derivatization enabling absolute configuration determination through ECD computational analysis

Abstract

The stereoselective transformation of chiral UV-transparent amines and alcohols to phthalimides has proved to be a simple and efficient method to enhance the chiroptical response of these substrates allowing their reliable absolute configuration determination by computational analysis of ECD spectra. Such a transformation also leads to a significant reduction in the molecular conformational flexibility thus simplifying the conformational analysis required by the computational treatment. The method described herein thus allows the absolute configuration assignment to these challenging substrates to be much easier and reliable.

Graphical abstract: Amplification of the chiroptical response of UV-transparent amines and alcohols by N-phthalimide derivatization enabling absolute configuration determination through ECD computational analysis

Supplementary files

Article information

Article type
Paper
Submitted
09 Jan 2020
Accepted
16 Feb 2020
First published
17 Feb 2020

Org. Biomol. Chem., 2020,18, 2094-2102

Amplification of the chiroptical response of UV-transparent amines and alcohols by N-phthalimide derivatization enabling absolute configuration determination through ECD computational analysis

D. Padula, G. Mazzeo, E. Santoro, P. Scafato, S. Belviso and S. Superchi, Org. Biomol. Chem., 2020, 18, 2094 DOI: 10.1039/D0OB00052C

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