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Updated: May 21, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Simple and efficient methods for discrimination of chiral diacids and chiral alpha-methyl amines
Sachin R Chaudhari1, N Suryaprakash
1NMR Research Center and Solid State and Structural Chemistry Unit Indian Institute of Science, Bangalore-560012, India.
Abstract:
The three-component chiral derivatization protocols have been developed for (1)H, (13)C and (19)F NMR spectroscopic discrimination of chiral diacids by their coordination and self-assembly with optically active (R)-α-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 (1)H and (19)F 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.
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