Letters in Peptide Science

, Volume 7, Issue 3, pp 165–169 | Cite as

Convenient and simple homologation ofN α-urethane protected α-amino acids to their β-homologues with concomitant pentafluorophenyl ester formation

  • Hosahudya N. Gopi
  • Vommina V. Suresh Babu
Article

Summary

The Wolff rearrangement of α-aminodiazoketones derived fromN α-urethane protected α-amino acids in the presence of pentafluorophenol catalyzed by silver acetate at low temperature results in the homologation of Fmoc-/Boc-/Z-α-amino acids to β-amino acids with concomitant formation of the corresponding pentafluorophenyl esters in good yield and purity.

Key words

α-aminodiazoketones concomitant ester formation ketene trapping pentafluorophenol 

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Copyright information

© Kluwer Academic Publishers 2000

Authors and Affiliations

  • Hosahudya N. Gopi
    • 1
  • Vommina V. Suresh Babu
    • 1
  1. 1.Department of Studies in ChemistryBangalore UniversityBangaloreIndia

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