Niobium(V) chloride-catalyzed C-H insertion reactions of α-diazoesters: synthesis of β-keto esters

J.S. Yadav*, B.V. Subba Reddy, B. Eeshwaraiah and P.N. Reddy

*Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India, Email: jsyadaviict.res.in

J. S. Yadav, B. V. S. Reddy, B. Eeshwaraiah, P. N. Reddy, Tetrahedron, 2005, 61, 875-878.

DOI: 10.1016/j.tet.2004.11.027

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Abstract

Aldehydes react readily with ethyl diazoacetate in the presence of 5 mol% of NbCl₅ in dichloromethane to produce the corresponding β-keto esters in good yields with high selectivity. This method allows the preparation of β-keto esters from various aldehydes under mild reaction conditions.

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proposed mechanism

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Bi(OTf)3-[Bmim]PF6: A novel and Reusable Catalytic System for the Synthesis of cis-Aziridine Carboxylates

J. S. Yaday, B. V. S. Reddy, P. N. Reddy, M. Shesha Rao, Synthesis, 2003, 1387-1389.

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Key Words

Transition metal catalysis, Carbene insertion, Diazo esters, β-Keto esters

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ID: J72-Y2005-2800