Asymmetric Synthesis of Alpha-Amino Acid Benzyl Esters via the Bisbenzyl Bislactim Ether of cyclo(-L-Val-Gly-)

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Asymmetric_Synthesis_of_Alpha.pdf
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1993
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Schmeck, Carsten
Schöllkopf, Ulrich
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Zusammenfassung

The diketopiperazine cyclo(-L-Val-Gly-) (1) can be 0-alkylated under mild acidic reaction conditions with the alkyl trichloroacetimidates 2 to the corresponding bisalkyl bislactim ethers. Alkylation of the bisbenzyl bislactim ether anion of cyclo(-L-Val-Gly-) 4 c with benzyl bromide and subsequent hydrolysis with aqueous trifluoroacetic acid afforded D-phenyl-alanine benzyl ester (8) with an enantiomeric excess of >95%.

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540 Chemie
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Peptides, Amino acids, Trichloroacetimidates, Bislactim ether method
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ISO 690GROTH, Ulrich, Carsten SCHMECK, Ulrich SCHÖLLKOPF, 1993. Asymmetric Synthesis of Alpha-Amino Acid Benzyl Esters via the Bisbenzyl Bislactim Ether of cyclo(-L-Val-Gly-). In: Liebigs Annalen der Chemie. 1993, 1993(3), pp. 321-323. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199319930153
BibTex
@article{Groth1993Asymm-9926,
  year={1993},
  doi={10.1002/jlac.199319930153},
  title={Asymmetric Synthesis of Alpha-Amino Acid Benzyl Esters via the Bisbenzyl Bislactim Ether of cyclo(-L-Val-Gly-)},
  number={3},
  volume={1993},
  issn={0170-2041},
  journal={Liebigs Annalen der Chemie},
  pages={321--323},
  author={Groth, Ulrich and Schmeck, Carsten and Schöllkopf, Ulrich}
}
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