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

J. S. Yadav*, B. V. S. Reddy, P. N. Reddy, M. Shesha Rao

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

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

DOI: 10.1055/s-2003-40212

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Abstract

Aldimines (generated in situ from aldehydes and amines) react readily with ethyl diazoacetate in the presence of 2 mol% of Bi(OTf)₃ in [bmim]PF₆ to produce the corresponding aryl aziridine carboxylates in high yields with excellent cis-diastereoselectivity.

see article for more examples

proposed mechanism

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

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

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Key Words

Darzens Reaction, aldimines, aziridine carboxylates, aziridines, metal triflates, ionic liquids, multicomponent reactions

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ID: J66-Y2003-1880