Practical, asymmetric synthesis of aromatic-substituted bulky and hydrophobic tryptophan derivatives

Wei Wang, Chiyi Xiong, Jianqing Yang, Victor J Hruby

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

An efficient method for the synthesis of novel aromatic substituted, bulky and hydrophobic tryptophan derivatives has been developed. Asymmetric hydrogenations of α-enamide 5 using Burk's DuPHOS-based catalysts generated high enantiomerically pure D- and L-α-amino acid derivatives 6, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford aromatic substituted tryptophan derivatives 7 and 8 in high yields. The method can allow for the preparation of such amino acids in large-scales for extensive structure-activity studies.

Original languageEnglish (US)
Pages (from-to)7717-7719
Number of pages3
JournalTetrahedron Letters
Volume42
Issue number44
DOIs
StatePublished - Oct 29 2001

Fingerprint

Tryptophan
Boronic Acids
Derivatives
Amino Acids
Hydrogenation
Catalysts

Keywords

  • Amino acids
  • Asymmetric hydrogenation
  • Suzuki cross coupling
  • Tryptophan

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Practical, asymmetric synthesis of aromatic-substituted bulky and hydrophobic tryptophan derivatives. / Wang, Wei; Xiong, Chiyi; Yang, Jianqing; Hruby, Victor J.

In: Tetrahedron Letters, Vol. 42, No. 44, 29.10.2001, p. 7717-7719.

Research output: Contribution to journalArticle

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