Facile Synthesis of Aryl α-Keto Esters via the Reaction of Aryl Diazoacetate with H₂O and DEAD

Zhenqiu Guo, Haoxi Huang, Qingquan Fu, Wenhao Hu*

*Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P. R. of China, Email: huwhcioc.ac.cn

Z. Guo, H. Huang, Q. Fu, W. Hu, Synlett, 2006, 2486-2488.

DOI: 10.1055/s-2006-950412

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Abstract

The reaction of aryl diazoacetates with H₂O and diethyl azodicarboxylate (DEAD) catalyzed by dirhodium acetate gives aryl α-keto esters in high yields.

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proposed mechanism

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Key Words

α-keto esters, α-diazoacetates, oxonium ylides, fragmentation, diethyl azodicarboxylate

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ID: J60-Y2006-4630