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

Authors :
Padula D
Mazzeo G
Santoro E
Scafato P
Belviso S
Superchi S
Source :
Organic & biomolecular chemistry [Org Biomol Chem] 2020 Mar 18; Vol. 18 (11), pp. 2094-2102.
Publication Year :
2020

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.

Details

Language :
English
ISSN :
1477-0539
Volume :
18
Issue :
11
Database :
MEDLINE
Journal :
Organic & biomolecular chemistry
Publication Type :
Academic Journal
Accession number :
32107518
Full Text :
https://doi.org/10.1039/d0ob00052c