Synthesis of Functionalized Azomethine Ylides via the Rh(II)-Catalyzed Cyclization of α-Diazo Carbonyls onto Imino π-Bonds. -On the basis of a variety of reactions is shown that α-diazo carbonyl compounds containing an imino group in the γ-position undergo Rh(II)-catalyzed cyclization to produce azomethine ylides. Cycloaddition of these dipoles with different dipolarophiles such as ( II), (VII) and N-phenylmaleimide affords cycloadducts in good yields. The cyclization reaction is markedly dependent on the geometry about the imino π-bond (necessary E-configuration) as well as the basicity of the electron pair on the N-atom (e.g. no cyclization of aromatic isoxazole analogues of (X)). -(PADWA, A.; DEAN, D. C.; OSTERHOUT, M. H.; PRECEDO, L.; SEMONES, M. A.; J.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.