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: norbert.sewald
uni-bielefeld.de
A. Müller, C. Vogt, N. Sewald, Synthesis, 1998, 837-841.
DOI: 10.1055/s-1998-2075
Abstract
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.
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Key Words
Fmoc-β-Homoamino Acids, β-Amino Acids, Arndt-Eister Synthesis, Wolff Rearrangement, Sonochemistry, capillary zone electrophoresis
ID: J66-Y1998-530
