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Issue 3, 2014
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In situ approach for testing the enantiopurity of chiral amines and amino alcohols by 1H NMR

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Abstract

An in situ approach involving a simple mix and shake method for testing the enantiopurity of primary, secondary and tertiary chiral amines and their derivatives, chiral amino alcohols, by 1H-NMR spectroscopy is developed. The protocol involves the in situ formation of chiral ammonium borate salt from a mixture of C2 symmetric chiral BINOL, trialkoxyborane and chiral amines. The proposed concept was demonstrated convincingly on a large number of chiral and pro-chiral amines and amino alcohols, and also aids the precise measurement of enantiomeric excess. The protocol can be completed in a couple of minutes directly in the NMR sample tube, without the need for any physical separation.

Graphical abstract: In situ approach for testing the enantiopurity of chiral amines and amino alcohols by 1H NMR

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Publication details

The article was received on 15 Aug 2013, accepted on 17 Oct 2013, published on 17 Oct 2013 and first published online on 17 Oct 2013


Article type: Paper
DOI: 10.1039/C3OB41671B
Citation: Org. Biomol. Chem., 2014,12, 495-502
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    In situ approach for testing the enantiopurity of chiral amines and amino alcohols by 1H NMR

    S. K. Mishra, S. R. Chaudhari and N. Suryaprakash, Org. Biomol. Chem., 2014, 12, 495
    DOI: 10.1039/C3OB41671B

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