1,2-Aryl and 1,2-Hydride Migration in Transition Metal Complex Catalyzed Diazo Decomposition:  A Novel Approach to α-Aryl-β-enamino Esters

Nan Jiang, Zhaohui Qu and Jianbo Wang*

*Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemistry, Peking University, Beijing 100871, China, Email: wangjbpku.edu.cn

N. Jiang, Z. Qu, J. Wang, Org. Lett., 2001, 3, 2989-2992.

DOI: 10.1021/ol016324p

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Abstract

N-Tosyl diazoketamines were prepared by addition of the ethyl α-diazoacetate anion to N-sulfonylimines. A subsequent diazo decomposition of the diazoketamines with Rh₂(OAc)₄ as catalyst provided α-aryl-β-enamino esters in good yields and high stereoselectivity via aryl migration.

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proposed mechanism

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Key Words

Diazo Compounds, Enamines, Migration

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ID: J54-Y2001