A versatile route towards 6-arylpipecolic acids
Erich Gebel, Cornelia Göcke, Carolin Gruner, Norbert Sewald
TL;DR
This paper introduces a new method to create enantiomerically pure pipecolic acid derivatives with aryl groups in the C6 position using chiral amino acids and metal-catalyzed reactions.
Contribution
A novel route for synthesizing 6-arylpipecolic acids using chiral amino acids and transition metal-catalyzed cross-coupling.
Findings
Enantiomerically pure pipecolic acid derivatives with aryl modifications in C6 position were successfully synthesized.
NMR analysis revealed conformational constraints and dihedral angles consistent with coupling constants.
The method utilizes a chiral pool and transition metal catalysis for efficient synthesis.
Abstract
Pipecolic acid is known as a non-proteinogenic amino acid with a secondary amine. It contains a six-membered ring and is, like its five-membered correlate, known for its secondary structure inducing properties, which are particularly useful in the design of peptide conformations. We present a new and improved way to generate enantiomerically pure pipecolic acid derivatives with aryl modifications in C6 position by utilising the chiral pool of a non-proteinogenic amino acid in combination with transition metal-catalysed cross-coupling reactions. Moreover, we present an in-depth NMR analysis of the key intermediate steps, which illustrates the conformational constraints in accordance with coupling constants and resulting dihedral angles.
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Taxonomy
TopicsChemical Synthesis and Analysis · Asymmetric Synthesis and Catalysis · Synthetic Organic Chemistry Methods