Simple Preparation of α-Diazo Esters

Douglass F. Taber,* Ritesh B. Sheth and Pramod V. Joshi

*Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, Email: taberdfudel.edu

D. F. Taber, R. B. Sheth, P. V. Joshi, J. Org. Chem., 2005, 70, 2851-2854.

DOI: 10.1021/jo048011o (free Supporting Information)

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Abstract

The TiCl₄-mediated reaction of esters with benzoyl chloride gave α-benzoylated esters in high yields. Diazo transfer of the α-benzoylated esters utilizing p-acetoamidobenzenesulfonyl azide afforded α-diazo esters in good yields. This procedure allows the preparation of α-diazo esters in gram quantities.

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Key Words

β-Keto Esters, α-Diazo Ester, α-Amination

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ID: J42-Y2005-360