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Simple and efficient methods for discrimination of chiral diacids and chiral alpha-methyl amines

Chaudhari, SachinR and Suryaprakash, N (2012) Simple and efficient methods for discrimination of chiral diacids and chiral alpha-methyl amines. In: ORGANIC & BIOMOLECULAR CHEMISTRY, 10 (31). pp. 6410-6419.

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Official URL: http://dx.doi.org/10.1039/c2ob25599e

Abstract

The three-component chiral derivatization protocols have been developed for H-1, C-13 and F-19 NMR spectroscopic discrimination of chiral diacids by their coordination and self-assembly with optically active (R)-alpha-methylbenzylamine and 2-formylphenylboronic acid or 3-fluoro-2-formylmethylboronic acid. These protocols yield a mixture of diastereomeric imino-boronate esters which are identified by the well-resolved diastereotopic peaks with significant chemical shift differences ranging up to 0.6 and 2.1 ppm in their corresponding H-1 and F-19 NMR spectra, without any racemization or kinetic resolution, thereby enabling the determination of enantiopurity. A protocol has also been developed for discrimination of chiral alpha-methyl amines, using optically pure trans-1,2-cyclohexanedicarboxylic acid in combination with 2-formylphenylboronic acid or 3-fluoro-2-fluoromethylboronic acid. The proposed strategies have been demonstrated on large number of chiral diacids and chiral alpha-methyl amines.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to Royal Society of Chemistry
Department/Centre: Division of Chemical Sciences > NMR Research Centre (Formerly SIF)
Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited: 21 Aug 2012 04:00
Last Modified: 21 Aug 2012 04:02
URI: http://eprints.iisc.ernet.in/id/eprint/44970

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