A facile circular dichroism protocol for rapid determination of enantiomeric excess and concentration of chiral primary amines.

Chemistry : a European Journal
Sonia NietoEric V Anslyn

Abstract

A protocol for the rapid determination of the absolute configuration and enantiomeric excess (ee) of alpha-chiral primary amines with potential applications in asymmetric reaction discovery has been developed. The protocol requires derivatization of alpha-chiral primary amines through condensation with pyridine carboxaldehyde to quantitatively yield the corresponding imine. The Cu(I) complex with 2,2'-bis (diphenylphosphino)-1,1'-dinaphthyl (BINAP--Cu(I)) with the imine yields a metal-to-ligand charge-transfer (MLCT) band in the visible region of the circular dichroism (CD) spectrum upon binding. Diastereomeric host-guest complexes give CD signals of the same signs but different amplitudes, allowing for differentiation of enantiomers. Processing the primary optical data from the CD spectrum with linear discriminant analysis (LDA) allows for the determination of the absolute configuration and identification of the amines, and processing with a supervised multilayer perceptron artificial neural network (MLP-ANN) allows for the simultaneous determination of the ee and concentration. The primary optical data necessary to determine the ee of unknown samples is obtained in two minutes per sample. To demonstrate the utility of the pro...Continue Reading

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Citations

Dec 17, 2014·Journal of the American Society for Mass Spectrometry·Maureen E SmithDouglas S Masterson
May 19, 2016·Organic Letters·Huayin HuangHongjun Fan
Oct 5, 2016·Journal of the American Chemical Society·Zeus A De Los Santos, Christian Wolf
Jan 28, 2017·Journal of the American Chemical Society·Samantha L PilicerChristian Wolf
Jan 15, 2016·Organic & Biomolecular Chemistry·Zeus A De Los SantosChristian Wolf
Dec 1, 2018·Angewandte Chemie·Zeus A De Los SantosChristian Wolf
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Jun 28, 2019·Organic & Biomolecular Chemistry·Samantha L PilicerChristian Wolf
Jul 10, 2019·Chemistry : a European Journal·F Yushra ThanzeelChristian Wolf
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Sep 16, 2011·Chemistry : a European Journal·Lei YouEric V Anslyn
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Sep 9, 2010·The Journal of Organic Chemistry·Daniel P Iwaniuk, Christian Wolf
Nov 23, 2013·Journal of the American Chemical Society·Keith W BentleyChristian Wolf

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