Application of MCR: Facile one-pot diastereoselective syntheses of novel chiral α,α′-iminodiacetic acid analogues

Kuangsen Sung, Fu Lin Chen, Meng Jung Chung

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22 Citations (Scopus)

Abstract

Several pairs of enantiomeric α,α′-iminodiacetic acid analogues (2 and 4) were prepared separately by highly diastereoselective 3CR, which involves a reaction of an isocyanide, an aldehyde, and an enantiomerically pure amino acid in methanol. Synthesis of each of the enantiomers was controlled by the configuration of the amino acid; L-amino acid produces one enantiomer and D-amino acid generates the other. The diastereoselectivity of the 3CR is very sensitive to the substituent size of both aldehyde and enantiomerically pure amino acid.

Original languageEnglish
Pages (from-to)213-221
Number of pages9
JournalMolecular Diversity
Volume6
Issue number3-4
DOIs
Publication statusPublished - 2003

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Information Systems
  • Molecular Biology
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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