Synthesis of α-Diazoketones

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The chain extension of carboxylic acids developed by Arndt and Eistert was applied to the construction of peptides containing β-amino acids. The method may be used for the generation of new types of peptide-containing combinatorial libraries.
J. Podlech, D. Seebach, Angew. Chem. Int. Ed., 1995, 34, 471-472.

Reaction of trimethylsilyldiazomethane with a mixed anhydride derived from a carboxylic acid and ethyl chloroformate yields the corresponding diazoketone in high yield. Subsequent Wolff rearrangement of the diazoketone leads to the homologated ester. Reactions of trimethylsilyldiazomethane with convenient active esters are described.
J. Cesar, M. Sollner Dolenc, Tetrahedron Lett., 2001, 42, 7099-7102.

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.
A. Müller, C. Vogt, N. Sewald, Synlett, 2006, 837-841.

α-Aryl-α-diazo ketones derived from direct diazo transfer with α-aryl ketones cyclize efficiently in the presence of Rh catalysts to give the corresponding α-aryl cyclopentanones.
D. F. Taber, W. Tian, J. Org. Chem., 2007, 72, 3207-3210.