An efficient synthesis of (2S, 6S)- and meso-diaminopimelic acids via asymmetric hydrogenation

W. Wang, C. Xiong, J. Yang, Victor J Hruby

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

An efficient synthesis of the title compounds 1 and 2 has been successfully developed. The key step is the asymmetric hydrogenation of dehydroamino acid 7 using [Rh(I)(COD)-(S,S) or - (R,R)-Et-DuPHOS)]+OTf- to produce the optically active, protected amino acid derivatives in high ee (>95%). The approach also can be used for the synthesis of other isomers and analogues.

Original languageEnglish (US)
Pages (from-to)94-98
Number of pages5
JournalSynthesis
Issue number1
StatePublished - 2002

Fingerprint

Diaminopimelic Acid
Hydrogenation
Acids
Isomers
Amino acids
Derivatives
Amino Acids

Keywords

  • Amino acids
  • Asymmetric hydrogenation
  • DAP analogues
  • Diaminopimelic acids
  • DuPHOS

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

An efficient synthesis of (2S, 6S)- and meso-diaminopimelic acids via asymmetric hydrogenation. / Wang, W.; Xiong, C.; Yang, J.; Hruby, Victor J.

In: Synthesis, No. 1, 2002, p. 94-98.

Research output: Contribution to journalArticle

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