Organic Chemistry Portal



Synthesis of Fmoc-β-Homoamino Acids by Ultrasound-Promoted Wolff Rearrangement

Annett Müller, Carla Vogt, Norbert Sewald*

*Universität Bielefeld, Fakultät für Chemie, Organische und Bioorganische Chemie, Postfach 10 01 31, 33501 Bielefeld, Germany, Email:

A. Müller, C. Vogt, N. Sewald, Synthesis, 1998, 837-841.

DOI: 10.1055/s-1998-2075


Sonication of diazo ketones derived from Fmoc-protected amino acids in dioxane in the presence of silver benzoate and water results in clean formation of the corresponding β-amino acid derivatives. The degree of racemization was examined using capillary zone electrophoresis. No substantial epimerization occured except for phenylglycine.

see article for more examples

Key Words

Fmoc-β-Homoamino Acids, β-Amino Acids, Arndt-Eister Synthesis, Wolff Rearrangement, Sonochemistry, capillary zone electrophoresis

ID: J66-Y1998-530