Schöllkopf bis-lactim amino acid synthesis

What is Schöllkopf bis-lactim amino acid synthesis?

The Schöllkopf bis-lactim amino acid synthesis is a method used for producing asymmetric amino acids. It involves diastereoselective alkylation of the lithiated bis-lactim ether, which is obtained from L-Val and Gly or Ala, with an electrophile.

Schöllkopf bis-lactim amino acid synthesis

Subsequent acid hydrolysis then liberates L-Val-OCH3 and the (R)-α-substituted amino acid ester. Moreover, it should be noted that the (S)-enantiomer is obtained when the bis-lactim is generated from D-Val.

References

  • Schöllkopf, U., Hartwig, W. and Groth, U. (1979), Enantioselective Synthesis of α-Methyl-α-aminocarboxylic Acids by Alkylation of the Lactim Ether of cyclo-(L-Ala-L-Ala). Angew. Chem. Int. Ed. Engl., 18: 863-864. https://doi.org/10.1002/anie.197908631
  • Schöllkopf, U., Groth, U. and Deng, C. (1981), Enantioselective Syntheses of (R)-Amino Acids Using L-Valine as Chiral Agent. Angew. Chem. Int. Ed. Engl., 20: 798-799. https://doi.org/10.1002/anie.198107981
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