Chiral N-Fmoc-beta-amino alkyl isonitriles derived from amino acids: first synthesis and application in 1-substituted tetrazole synthesis

J Org Chem. 2009 Jan 2;74(1):153-7. doi: 10.1021/jo801527d.

Abstract

A novel class of optically active N-Fmoc-protected amino isonitriles has been described for the first time. Conversion of the carboxyl group of Fmoc-beta-amino acids into an isocyano group has resulted in a new class of N-urethane-protected amino isonitriles. All the isonitriles have been isolated as stable solids, purified, and completely characterized. A synthetic application of the obtained isonitriles has also been demonstrated through the synthesis of 1-substituted tetrazole analogues of amino acids via a 2 + 3 cycloaddition with trimethylsilyl azide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Azides / chemistry
  • Cyclization
  • Molecular Conformation
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry
  • Stereoisomerism
  • Tetrazoles / chemistry*
  • Trimethylsilyl Compounds / chemistry

Substances

  • Amino Acids
  • Azides
  • Nitriles
  • Tetrazoles
  • Trimethylsilyl Compounds