Chiral α ‐Amino Acid‐Based NMR Solvating Agents

Four new chiral α ‐(nonafluoro‐ tert ‐butoxy)carboxylic acids were synthesized from naturally occurring α ‐amino acids (alanine, valine, leucine and isoleucine, respectively), and tested in 1 H‐ and 19 F‐NMR experiments as chiral NMR shift reagents. The NMR studies were carried out at room temperature, using CDCl 3 and C 6 D 6 as solvents, and ( RS )‐ α ‐phenylethylamine and ( RS )‐ α ‐(1‐naphthyl)ethylamine as racemic model compounds. To demonstrate the applicability of the reagents, the racemic drugs ketamine and prasugrel were also tested.