Design and synthesis of hydrophobic, bulky χ2-constrained phenylalanine and naphthylalanine derivatives

Wei Wang, Junyi Zhang, Chiyi Xiong, Victor J. Hruby

Research output: Contribution to journalArticle

27 Scopus citations

Abstract

A series of novel hydrophobic, bulky χ2-constrained phenylalanine and naphthylalanine derivatives were designed and synthesized. Asymmetric hydrogenations of α-enamides using Burk's DuPHOS-based Rh(I) catalysts generated high enantiomerically pure α-amino acid derivatives, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford these aromatic substituted amino acids in high yields and with high enantioselectivity.

Original languageEnglish (US)
Pages (from-to)2137-2140
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number12
DOIs
StatePublished - Mar 18 2002

Keywords

  • Asymmetric hydrogenation
  • Constrained amino acids
  • DuPHOS
  • Naphthylalanine
  • Phenylalanine

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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