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Synthesis of α-Diazo Esters

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Diazo transfer of α-benzoylated esters utilizing p-acetoamidobenzenesulfonyl azide afforded α-diazo esters in good yields.
D. F. Taber, R. B. Sheth, P. V. Joshi, J. Org. Chem., 2005, 70, 2851-2854.


Various diazoacetates were synthesized from the corresponding bromoacetates by treatment with N,N'-ditosylhydrazine in moderate to high yields. Ease of operation with the stable crystalline reagent as well as a short reaction time offer a useful alternative to the conventional methods.
T. Toma, J. Shimokawa, T. Fukuyama, Org. Lett., 2007, 9, 3195-3197.