Analytical Letters

Exceptionally Simple Homologation of Protected α??to β??Amino Acids in the Presence of Silica Gel

K Koch, J Podlech

Index: Koch, Karen; Podlech, Joachim Synthetic Communications, 2005 , vol. 35, # 21 p. 2789 - 2794

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Citation Number: 12

Abstract

Abstract The Wolff rearrangement of α??amino acid–derived diazoketones is simply achieved by gentle warming in a ethyl acetate/silica gel slurry containing catalytic amounts of silver trifluoroacetate. Without workup (not counting filtration and evaporation) the protected β?? amino acids are obtained in high yields (92–97%) without significant impurities. This variation avoids the laborious workup after a conventional silver??catalyzed Wolff ...