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
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
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.
Key Words
Darzens Reaction, aldimines, aziridine carboxylates, aziridines, metal triflates, ionic liquids, multicomponent reactions
ID: J66-Y2003-1880