Chiral Auxiliary for the Synthesis of Optically Active Amino Acids

(S)-N-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide (1) is a chiral auxiliary agent used in the synthesis of optically active amino acids. When racemic α-amino acids as substrates react with 1 in presence of nickel nitrate and sodium methoxide, the isomerization at the α-position of the amino acids occurs via the formation of an intermediate 2. The hydrolysis of 2 by acid yields (S)-amino acids with high optical purity.¹⁾ When the nickel complex of 1 and glycine is treated with 3, the introduction of an alkyl group proceeds to give 4. Subsequent hydrolysis and protection with Fmoc-OSu affords N^α-Fmoc-ω-alkynyl-L-amino acids.²⁾

Related Products

P1737

[N-[α-[2-(Piperidinoacetamido)phenyl]benzylidene]glycinato]nickel

P1738

[N-[1-[2-(2-Pyridylcarboxamido)phenyl]ethylidene]glycinato]nickel

References

• 1) Optimisation of the retroracemisation procedure for α-amino acids using (S)-2-[(N-alkylprolyl)amino]benzophenones, recyclable chiral auxiliaries
  • B. B. De, N. R. Thomas, Tetrahedron Asymmetry 1997, 8, 2687.
• 2) N^α-Fmoc-Protected ω-Azido- and ω-Alkynyl-L-amino Acids as Building Blocks for the Synthesis of “Clickable” Peptides
  • A. L. C. Isaad, F. Barbetti, P. Rovero, A. M. D'Ursi, M. Chelli, M. Chorev, A. M. Papini, Eur. J. Org. Chem. 2008, 31, 5308.

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